Synthesis of 3,5-O-Benzylidene-2-deoxy-L-riboaldose from 5,5-Dihydroxy-2-phenyl-1,3-dioxane

The asymmetric alkylation of 2-phenyl-1,3-dioxan-5-one was achieved via the RAMP-hydrazone. Regeneration of the ketone followed by setreoselective reduction and ozonolysis, gave the protected 2-deoxy-L-ribose, 3,5-O-benzyldiene-2-deoxy-L-erythro-pentoaldose with 98% e.e. Removal of the benzylidene y...

Full description

Saved in:
Bibliographic Details
Published in:Synthetic communications 2000-07, Vol.30 (13), p.2275-2280
Main Authors: Ulven, Trond, Carlsen, Per H. J.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The asymmetric alkylation of 2-phenyl-1,3-dioxan-5-one was achieved via the RAMP-hydrazone. Regeneration of the ketone followed by setreoselective reduction and ozonolysis, gave the protected 2-deoxy-L-ribose, 3,5-O-benzyldiene-2-deoxy-L-erythro-pentoaldose with 98% e.e. Removal of the benzylidene yielded the unnatural 2-deoxy-L-ribose.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910008086866