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Coupling of Unprotected 2-Deoxy-D-ribose at C-3 as a New Route to 2,3-Dideoxy-3-phthalimido-D-pentoses

✍ Scribed by Motawia, Mohammed S. ;Nawwar, Galal A. M. ;Andreassen, Erik S. ;Jacobsen, Jens Peter ;Pedersen, Erik B.

Publisher: John Wiley and Sons
Year: 1987
Tongue: English
Weight: 401 KB
Volume: 1987
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198719870881

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✦ Synopsis

Direct condensation of 2-deoxy-i>-ribose (2) with phlhalirnides using P,O,&I:O/Bu~N rcagcnt in chloroform at 40°C results in ii coupling ai C-3 of the carbohydrate moiety to give an isomeric mix1 urc d2,3-dideoxy-3-phthrlimido-~-pentoses 3-5. Acetylation of 3b -5 b using acetic anhydride in dry pyridine givcs thc corrcsponding acctylated derivativcs 6-8. After Ireating thc mixture of 3b. 4b. and S b with triphcnylmcthyl chloride iii pyridine. pure heepyranose derivative 3b and purc tritylated cvylhro-furanose derivative 9 are obtained by fractional p r d piiation.

It is of great interest to find a convenient method for the synthesis of amino sugars because a great number of antibiotics with remarkably successful clinical applications contain the amino sugar moieties as an essential character '-' 1. Furthermore, the synthetic route to amino sugars is a complex multi-step reaction5 ' 1.

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