A stereodivergent approach to carbahexofuranoses: synthesis of carba-[alpha]-d-glucofuranose, carba-[beta]-d-altrofuranose, carba-[alpha]-d-allofuranose, carba-[beta]-d-idofuranose, carba-[alpha]-d-galactofuranose and carba-[beta]-d-talofuranose

A stereodivergent route, starting from d-glyceraldehyde derivative, employing Wittig olefination-Claisen rearrangement protocol is reported for the synthesis of six novel carbahexofuranoses-carba-[alpha]-d-glucofuranose, carba-[beta]-d-altrofuranose, carba-[alpha]-d-allofuranose, carba-[beta]-d-idof...

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Bibliographic Details
Published in:Tetrahedron letters 2011-10, Vol.52 (43), p.5559-5562
Main Authors: Kulkarni, Mukund G, Borhade, Ajit S, Shaikh, Yunnus B, Dhondge, Attrimuni P, Birhade, Deekshaputra R, Dhatrak, Nagorao R
Format: Article
Language:English
Subjects:
Derivatives
Synthesis (chemistry)
Tetrahedrons
Online Access:Get full text
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Summary:A stereodivergent route, starting from d-glyceraldehyde derivative, employing Wittig olefination-Claisen rearrangement protocol is reported for the synthesis of six novel carbahexofuranoses-carba-[alpha]-d-glucofuranose, carba-[beta]-d-altrofuranose, carba-[alpha]-d-allofuranose, carba-[beta]-d-idofuranose, carba-[alpha]-d-galactofuranose and carba-[beta]-d-talofuranose in enantiomerically pure form.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.08.006