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Preparation of methyl 4,6-di-O-acetyl-3-C-nitro-2-enopyranoside derivatives and their reduction with sodium borodeuteride

✍ Scribed by Akinori Seta; Kiohisa Tokuda; Miki Kaiwa; Tohru Sakakibara

Book ID: 102994037
Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 755 KB
Volume: 281
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00341-x

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✦ Synopsis

The conformationally flexible title compounds were prepared and subjected to reduction with sodium borodeuteride. Deuteride ion attacks exclusively from the side opposite of the anomeric methoxyl group. However, the stereoselectivity of a similar reduction of the corresponding 4,6-O-benzylidene-~-I>threo-2-enopyranoside derivative, adopting the °H 5 conformation, was exceptionally low, suggesting that reduction of the 4,6-diacetate having the ~-o-threo configuration did not occur from the stable °H 5 conformation, but from an unstable (SH 0) one.

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