Title:
STEREOSELECTIVE SYNTHESIS METHOD FOR 4'-SUBSTITUTED NUCLEOSIDE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2020/032152
Kind Code:
A1
Abstract:
Current synthesis methods for 4'-substituted nucleoside derivatives include a step in which stereoisomers are produced and therefore have problems such as decreased yield and complication of a refinement step. Thus, a synthesis method has been sought that is simpler and does not produce stereoisomers. The present invention provides a synthesis method for a 4'-substituted nucleoside intermediate represented by formula (6), the method comprising the following steps 1 through 3: step 1 in which a compound of formula (3) is used as a starting raw material, and a nucleophile is made to act on the compound of formula (3) to obtain the compound of formula (4) in which a substituent group has been stereoselectively introduced; step 2 in which the compound of formula (4) is hydrolized to obtain the compound of formula (5); and step 3 in which the compound of formula (5) is held in acidic conditions to obtain the compound represented by formula (6). In the formulas, R1 indicates a protective group of a hydroxyl group, Me indicates a methyl group, and X indicates a substituent group.
Inventors:
KOHGO SATORU (JP)
MATSUURA TOMOKO (JP)
MATSUURA TOMOKO (JP)
Application Number:
PCT/JP2019/031293
Publication Date:
February 13, 2020
Filing Date:
August 08, 2019
Export Citation:
Assignee:
YAMASA CORP (JP)
International Classes:
C07H15/04; C07H1/00; C07H19/067
Foreign References:
| JP2015523337A | 2015-08-13 | |||
| JP2001335593A | 2001-12-04 | |||
| JPH11349596A | 1999-12-21 | |||
| JPH09328497A | 1997-12-22 |
Other References:
ORTIZ, A. ET AL.: "Scalable Synthesis of the Potent HIV Inhibitor BMS-986001 by Non-Enzymatic Dynamic Kinetic Asymmetric Transformation(DYKAT", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 54, no. 24, 2015, pages 7185 - 7188, XP055654660
WAGA, T. ET AL.: "Synthesis of 4'-C-Methylnucleosides", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 57, no. 9, 1993, pages 1433 - 1438, XP000917028
WAGA, T. ET AL.: "Synthesis of 4'-C-Methylnucleosides", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 57, no. 9, 1993, pages 1433 - 1438, XP000917028
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