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Synthesis of a 2-deoxy-ribose type 1-N-iminosugar

✍ Scribed by Kazuishi Makino; Yoshitaka Ichikawa

Book ID
104260047
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
247 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A 2-deoxy-ribose-type 1-N-iminosugar 5 was synthesized, in multi-gram scale, from fumaric acid monoethyl ester employing Sharpless asymmetric epoxidation followed by a Lewis acid-catalyzed (Yamamoto's aluminum reagent) cyanide epoxy ring-opening reactions.

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## For introducing 14C into position I of 2-deoxyaldoses, methods based on prolongation of the carbon chain usually come into consideration since one can proceed from simple and inexpensive 14C-compounds. Such a possibility is ofleered by the method of Fisher and Sowden'l? 2, which was applied by