AR036207A1 - 3,5-DIHIDROXI-2,2-DIMETIL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES, A PROCEDURE FOR THEIR PREPARATION AND THE USE OF THEMSELVES - Google Patents
3,5-DIHIDROXI-2,2-DIMETIL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES, A PROCEDURE FOR THEIR PREPARATION AND THE USE OF THEMSELVESInfo
- Publication number
- AR036207A1 AR036207A1 ARP020102940A ARP020102940A AR036207A1 AR 036207 A1 AR036207 A1 AR 036207A1 AR P020102940 A ARP020102940 A AR P020102940A AR P020102940 A ARP020102940 A AR P020102940A AR 036207 A1 AR036207 A1 AR 036207A1
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- compounds
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- benzyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se describen 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas de fórmula general (1) en donde R1, R2 pueden ser iguales o diferentes y representan, independientemente entre sí, un grupo protector de alcohol tal como, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, grupo (2); Y representa un grupo -NA1A2, en donde A1 y A2 representan independientemente un radical alquilo C1-6 tal como metilo, etilo, propilo, o un radical arilo o aralquilo tal como fenilo o bencilo, -OH, OMe u -O- bencilo, o representa un resto (3). También se describen antípodas ópticamente puros de los compuestos de fórmula (1), los productos intermedios, ópticamente activos, y compuestos de partida empleados en la preparación de los compuestos de fórmula (1), así como los procedimientos de preparación de todos estos compuestos. También se describe un procedimiento para preparar cetonas de fórmula general (4), donde R1, R2 pueden ser iguales o diferentes y representan independientemente un grupo protector de alcohol tal como, por ejemplo, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, por ejemplo, grupo (2) y V representa un radical alquilo C1-5 o alquenilo, a partir de compuestos de fórmula (1), ópticamente activos. Asimismo se describe el uso de estos compuestos para la obtención de epotilonas o derivados de epotilonas, en particular para la preparación del fragmento constitutivo (4) en la síntesis total de epotilonas. Los compuestos descriptos más arriba son estables al almacenamiento y pueden ser obtenidos fácilmente a partir de materiales de partida relativamente económicos. En general, son sustancias sólidas cristalinas y pueden purificarse por recristalización. De esta manera se pueden alcanzar elevados rendimientos químicos y ópticos.Protected 3,5-dihydroxy-2,2-dimethyl-valeroamides of general formula (1) are described in which R1, R2 may be the same or different and independently represent one another, an alcohol protecting group such as benzyl, 4 -methoxybenzyl, 3,4-dimethoxybenzyl, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, allyl, trityl, or in case R1 and R2 form a bridge, they represent a ketal protective group such as, group (two); Y represents a -NA1A2 group, wherein A1 and A2 independently represent a C1-6 alkyl radical such as methyl, ethyl, propyl, or an aryl or aralkyl radical such as phenyl or benzyl, -OH, OMe or -O-benzyl, or represents a remainder (3). Optically pure antipodes of the compounds of formula (1), intermediates, optically active, and starting compounds used in the preparation of the compounds of formula (1), as well as the methods of preparing all these compounds are also described. A process for preparing ketones of the general formula (4) is also described, where R1, R2 may be the same or different and independently represent an alcohol protecting group such as, for example, benzyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, allyl, trityl, or if R1 and R2 form a bridge, represent a ketal protective group such as, for example, group (2) and V represents a C1-5 alkyl or alkenyl radical, from compounds of formula (1), optically active. The use of these compounds for the preparation of epothilones or derivatives of epothilones is also described, in particular for the preparation of the constituent fragment (4) in the total synthesis of epothilones. The compounds described above are storage stable and can easily be obtained from relatively inexpensive starting materials. In general, they are crystalline solid substances and can be purified by recrystallization. In this way, high chemical and optical yields can be achieved.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10138348A DE10138348A1 (en) | 2001-08-03 | 2001-08-03 | Protected 3,5-dihydroxy-2,2-dimethyl-valeroamides for the synthesis of epothilones and derivatives and methods of preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR036207A1 true AR036207A1 (en) | 2004-08-18 |
Family
ID=7694415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020102940A AR036207A1 (en) | 2001-08-03 | 2002-08-02 | 3,5-DIHIDROXI-2,2-DIMETIL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES, A PROCEDURE FOR THEIR PREPARATION AND THE USE OF THEMSELVES |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1412322A2 (en) |
| JP (1) | JP2004537589A (en) |
| KR (1) | KR20040029394A (en) |
| CN (2) | CN1807403A (en) |
| AR (1) | AR036207A1 (en) |
| BR (1) | BR0211649A (en) |
| CA (1) | CA2456255A1 (en) |
| DE (1) | DE10138348A1 (en) |
| IL (1) | IL160159A0 (en) |
| MX (1) | MXPA04000954A (en) |
| NO (1) | NO20040912L (en) |
| PE (1) | PE20030345A1 (en) |
| PL (1) | PL367430A1 (en) |
| RU (1) | RU2004106530A (en) |
| WO (1) | WO2003014063A2 (en) |
| ZA (1) | ZA200401727B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69734362T2 (en) | 1996-12-03 | 2006-07-20 | Sloan-Kettering Institute For Cancer Research | SYNTHESIS OF EPOTHILONES, INTERMEDIATE PRODUCTS, ANALOGUES AND USES THEREOF |
| US6867305B2 (en) | 1996-12-03 | 2005-03-15 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| US6204388B1 (en) | 1996-12-03 | 2001-03-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| WO2003029195A1 (en) | 2001-09-28 | 2003-04-10 | Sumika Fine Chemicals Co., Ltd. | Intermediates for epothilone derivative and process for producing these |
| US6921769B2 (en) | 2002-08-23 | 2005-07-26 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| DE10326195A1 (en) | 2003-06-07 | 2004-12-23 | Schering Ag | Protected 5,7-dihydroxy-4,4-dimethyl-3-oxoheptanoic acid esters and 5,7-dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptanoic acid esters for the synthesis of epothilones and derivatives and processes for the preparation of these esters |
| CN110857276B (en) * | 2018-08-22 | 2021-03-02 | 中国科学院化学研究所 | A class of chiral β-hydroxyamide compounds, preparation method and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4824980A (en) * | 1988-09-02 | 1989-04-25 | Dow Corning Corporation | Process to produce O-silyl O,N-ketene acetals |
| US6211412B1 (en) * | 1999-03-29 | 2001-04-03 | The University Of Kansas | Synthesis of epothilones |
-
2001
- 2001-08-03 DE DE10138348A patent/DE10138348A1/en not_active Withdrawn
-
2002
- 2002-08-02 PE PE2002000704A patent/PE20030345A1/en not_active Application Discontinuation
- 2002-08-02 AR ARP020102940A patent/AR036207A1/en unknown
- 2002-08-05 KR KR10-2004-7001710A patent/KR20040029394A/en not_active Ceased
- 2002-08-05 JP JP2003519015A patent/JP2004537589A/en active Pending
- 2002-08-05 CN CNA2005100764590A patent/CN1807403A/en active Pending
- 2002-08-05 CA CA002456255A patent/CA2456255A1/en not_active Abandoned
- 2002-08-05 RU RU2004106530/04A patent/RU2004106530A/en not_active Application Discontinuation
- 2002-08-05 IL IL16015902A patent/IL160159A0/en unknown
- 2002-08-05 BR BR0211649-9A patent/BR0211649A/en not_active IP Right Cessation
- 2002-08-05 MX MXPA04000954A patent/MXPA04000954A/en unknown
- 2002-08-05 EP EP02774500A patent/EP1412322A2/en not_active Withdrawn
- 2002-08-05 PL PL02367430A patent/PL367430A1/en unknown
- 2002-08-05 WO PCT/EP2002/008726 patent/WO2003014063A2/en not_active Ceased
- 2002-08-05 CN CNA028152379A patent/CN1538952A/en active Pending
-
2004
- 2004-03-02 NO NO20040912A patent/NO20040912L/en not_active Application Discontinuation
- 2004-03-02 ZA ZA200401727A patent/ZA200401727B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL367430A1 (en) | 2005-02-21 |
| CA2456255A1 (en) | 2003-02-20 |
| RU2004106530A (en) | 2005-07-27 |
| CN1807403A (en) | 2006-07-26 |
| WO2003014063A2 (en) | 2003-02-20 |
| EP1412322A2 (en) | 2004-04-28 |
| IL160159A0 (en) | 2004-07-25 |
| NO20040912L (en) | 2004-03-02 |
| JP2004537589A (en) | 2004-12-16 |
| KR20040029394A (en) | 2004-04-06 |
| BR0211649A (en) | 2004-07-13 |
| WO2003014063A3 (en) | 2003-05-01 |
| PE20030345A1 (en) | 2003-04-10 |
| DE10138348A1 (en) | 2003-02-27 |
| ZA200401727B (en) | 2005-04-12 |
| CN1538952A (en) | 2004-10-20 |
| MXPA04000954A (en) | 2004-04-20 |
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