An improved route to 1,2-dideoxy-beta-1-phenyl-D-ribofuranose

Authors
Wichai, U Woski, SA
Citation
U. Wichai et Sa. Woski, An improved route to 1,2-dideoxy-beta-1-phenyl-D-ribofuranose, BIOORG MED, 8(24), 1998, pp. 3465-3468
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
8
Issue
24
Year of publication
1998
Pages
3465 - 3468
Database
ISI
SICI code
0960-894X(199812)8:24<3465:AIRT1>2.0.ZU;2-L
Abstract
An efficient synthesis of the aryl nucleoside analogue 1,2-dideoxy-beta-1-p henyl-D-ribofuranose (1) is described. This route utilizes the addition of phenyllithium to a protected 2-deoxyribonolactone followed by reduction wit h triethylsilane/boron trifluoride etherate to selectively produce the p-an omer. Deprotection yields the desired aryl C-nucleoside in 27% overall yiel d from 2-deoxy-D-ribose. (C) 1998 Elsevier Science Ltd. All rights reserved .