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Novel synthesis of 3-acetamido-3-deoxy- and 4-acetamido-4-deoxy-d-altrose from levoglucosenone using regioselective cis-oxyamination

✍ Scribed by Katsuya Matsumoto; Takashi Ebata; Hajime Matsushita

Book ID: 102995102
Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 859 KB
Volume: 267
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(94)00298-t

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✦ Synopsis

Two rare amino sugars, 3-acetamido-3-deoxy-and 4-acetamido-4-deoxy-D-altrose, were prepared from levoglucosenone (1,6-anhydro-3,4-dideoxy-fl-D-glycero-hex-3-enopyranos-2-ulose) respectively by reduction of the carbonyl group, selective cis-oxyamination of the carbon-carbon double bond, detosylation of the p-toluenesulfonamido group, acetylation, acetolysis of the 1,6anhydro bond, and finally deacetylation of the O-acetyl groups. The regioselectivity in cisoxyamination of the carbon-carbon double bond of allylic alcohol obtained by reduction of levoglucosenone could be controlled by the choice of the protecting groups of the allylic hydroxyl group.

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