SYNTHESIS OF 2-DEOXY-3,5-DI-O-BENZOYL-2,2-DIFLUORO-D-RIBOSE FROM D-GLUCOSE AND D-MANNOSE - A FORMAL SYNTHESIS OF GEMCITABINE

Authors
FERNANDEZ R MATHEU MI ECHARRI R CASTILLON S
Citation
R. Fernandez et al., SYNTHESIS OF 2-DEOXY-3,5-DI-O-BENZOYL-2,2-DIFLUORO-D-RIBOSE FROM D-GLUCOSE AND D-MANNOSE - A FORMAL SYNTHESIS OF GEMCITABINE, Tetrahedron, 54(14), 1998, pp. 3523-3532
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
14
Year of publication
1998
Pages
3523 - 3532
Database
ISI
SICI code
0040-4020(1998)54:14<3523:SO2FD>2.0.ZU;2-#
Abstract
The title compound 2-Deoxy-3,5-di-O-benzoyl-2,2-difluoro-D-ribose (17) , was synthesised from D-glucose and from D-mannose. The key steps of the synthesis from D-glucose are obtaining the 3,3-difluoropyranose 9 by reacting the ulose 7 with DAST. and their conversion into the diflu orofuranoside 17 by a degradative reaction of diol 16. Starting from D -mannose the synthesis obtains the 3,3-difluoroglycal 22 by reaction o f the ulose 18 with DAST and oxidation-elimination of selenoglycoside 21. Ozonolysis of 22 gives the difluorofuranose 17. (C) 1998 Elsevier Science Ltd. All rights reserved.