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WO1998039347A3 - Synthesis of l-ribose and 2-deoxy l-ribose - Google Patents

Synthesis of l-ribose and 2-deoxy l-ribose Download PDF

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Publication number
WO1998039347A3
WO1998039347A3 PCT/US1998/004302 US9804302W WO9839347A3 WO 1998039347 A3 WO1998039347 A3 WO 1998039347A3 US 9804302 W US9804302 W US 9804302W WO 9839347 A3 WO9839347 A3 WO 9839347A3
Authority
WO
WIPO (PCT)
Prior art keywords
ribose
deoxy
yield
converted
hydrolysis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1998/004302
Other languages
French (fr)
Other versions
WO1998039347A2 (en
Inventor
Michael E Jung
Yue Xu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of California Berkeley
University of California San Diego UCSD
Original Assignee
University of California Berkeley
University of California San Diego UCSD
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of California Berkeley, University of California San Diego UCSD filed Critical University of California Berkeley
Priority to AU66866/98A priority Critical patent/AU6686698A/en
Publication of WO1998039347A2 publication Critical patent/WO1998039347A2/en
Publication of WO1998039347A3 publication Critical patent/WO1998039347A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

A method for synthesizing L-ribose (1) and 2-deoxy L-ribose (12) from inexpensive D-ribose (2) is provided. The 5-O-trityl ribose (3) (prepared in 70 % yield from D-ribose) is reduced with borohydride to give the tetrol (4), which is then peracetylated to the tetraacetate (5). Hydrolysis of the trityl ether followed by Swern oxidation affords the aldehyde (7) via the alcohol (6). This aldehyde is a protected form of L-ribose, being L-ribose 2,3,4,5,-tetraacetate. Mild basic hydrolysis of the acetate affords L-ribose itself (1), thus ending an efficient six-step synthesis of (1) from (2) which proceeds in 39 % overall yield. In a second aspect of the invention, L-ribose is converted into the β-selenophenyl ribofuranoside (10) via the tetraester (9) in 71 % isolated yield for the four steps. Treatment of (10) with tributylstannane and AIBN furnishes in 84 % yield the tribenzoyl 2-deoxy-L-ribofuranoside (11) which, on basic hydrolysis, gives 2-deoxy L-ribose (12) in high yield. In a third aspect of the invention, L-arabinose (13) is converted into 2-deoxy L-ribose (12) via the arabinopyranosyl bromide (14), via similar reductive rearrangement with tributylstannane to give the 2-deoxy ribopyranose tribenzoate (16). Hydrolysis yields 2-deoxy L-ribose. In a third aspect of the invention, L-arabinose is converted into 2-deoxy L-ribose by an alternate route.
PCT/US1998/004302 1997-03-05 1998-03-05 Synthesis of l-ribose and 2-deoxy l-ribose Ceased WO1998039347A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU66866/98A AU6686698A (en) 1997-03-05 1998-03-05 Synthesis of l-ribose and 2-deoxy l-ribose

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4027097P 1997-03-05 1997-03-05
US60/040,270 1997-03-05

Publications (2)

Publication Number Publication Date
WO1998039347A2 WO1998039347A2 (en) 1998-09-11
WO1998039347A3 true WO1998039347A3 (en) 1998-10-22

Family

ID=21910078

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/004302 Ceased WO1998039347A2 (en) 1997-03-05 1998-03-05 Synthesis of l-ribose and 2-deoxy l-ribose

Country Status (2)

Country Link
AU (1) AU6686698A (en)
WO (1) WO1998039347A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100426030B1 (en) * 2000-07-22 2004-04-03 (주) 한켐 Chirality conversion method in lactone sugar compounds
KR100440461B1 (en) * 2000-08-19 2004-07-15 (주) 한켐 Process for the preparation of L-ribose using 1,4-lactone
JP3942414B2 (en) * 2000-11-29 2007-07-11 三井化学株式会社 L-type nucleic acid derivative and synthesis method thereof
KR100449310B1 (en) * 2001-11-08 2004-09-18 주식회사 삼천리제약 preparation method of 2-deoxy-L-ribose
KR100433179B1 (en) * 2001-11-10 2004-05-27 주식회사 삼천리제약 Method for Producing 2-Deoxy-L-ribose
KR100446560B1 (en) * 2002-07-15 2004-09-04 주식회사 삼천리제약 Method for Producing 2-Deoxy-L-ribose
KR100849979B1 (en) 2006-12-06 2008-08-01 주식회사 삼천리제약 The preparation method of 2-deoxy-L-ribose
CN102108089B (en) * 2009-12-29 2013-10-02 唐传生物科技（厦门）有限公司 Preparation method of 2-deoxy-L-ribose
CN102153600B (en) * 2010-02-12 2016-09-14 何遂庆 The preparation method of 2-deoxidation-L-ribose
NL2007240C2 (en) * 2011-08-09 2013-02-12 Konink Co Peratie Cosun U A Sugar-based plasticizers.
CN107778334A (en) * 2016-08-26 2018-03-09 康普药业股份有限公司 A kind of preparation method of Sebivo key intermediate

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 108, no. 19, 9 May 1988, Columbus, Ohio, US; abstract no. 167793w, R.A.GAKHOKIDZE ET AL.: "Synthesis of 2-Deoxyribose." page 684; column 2; XP002066660 *
CHEMICAL ABSTRACTS, vol. 119, no. 25, 20 December 1993, Columbus, Ohio, US; abstract no. 271608c, J.KUBALA ET AL.: "Method of Preparing Optically Active 2-Deoxy-L-Ribose." page 1049; column 1; XP002066659 *
CHEMICAL ABSTRACTS, vol. 122, no. 5, 30 January 1995, Columbus, Ohio, US; abstract no. 56398r, J.KUBALA ET AL.: "Process for Preparing L-Ribose." page 1231; column 2; XP002066661 *
M.E.JUNG ET AL.: "Efficient Synthesis of L-Ribose and 2-Deoxy-L-Ribose from D-Ribose and L-Arabinose.", TETRAHEDRON LETTERS., vol. 38, no. 24, 1997, OXFORD GB, pages 4199 - 4202, XP004074789 *
ZH. ORG. KHIM., vol. 23, no. 5, 1987, pages 1126 - 1127 *

Also Published As

Publication number Publication date
WO1998039347A2 (en) 1998-09-11
AU6686698A (en) 1998-09-22

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