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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

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.
Publication status:
Published

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Authors


Estevez, AM More by this author
Soengas, RG More by this author
Estevez, JC More by this author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
19
Issue:
21
Pages:
2443-2446
Publication date:
2008-11-03
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:01bb79f1-fd68-4a4a-95d2-8f7a6d00b4c6
Source identifiers:
41011
Local pid:
pubs:41011
Language:
English

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