Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed Ferrier rearrangement of acetylated 2-nitroglycals | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

5923659

Reference Type

Journal Article

Title

Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed Ferrier rearrangement of acetylated 2-nitroglycals

Author(s)

Dharuman, S; Gupta, P; Kancharla, PK; Vankar, YD

Year

2013

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Volume

Issue

Page Numbers

8442-8450

Language

English

PMID

23931299

DOI

10.1021/jo401165y

Web of Science Id

WOS:000330159300023

Abstract

A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-D-lividosaminide.