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Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol

Journal article published in 2008 by Jm Otero, Am Estevez, Rg Soengas ORCID, Jc Estevez ORCID, Rj Nash, George W. J. Fleet, Fleet Gwj, Rj Estevez
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyl)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-d-glucofuranose with formaldehyde followed by a reductive ring closure to give the first branched 1,6-dideoxy-1,6-heptitol described. © 2008 Elsevier Ltd. All rights reserved.