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Synthesis of nitrogen-15-labeled amino sugar derivatives by addition of phthalimide-15N to a carbohydrate epoxide

✍ Scribed by Bruce Coxon; Robert C. Reynolds

Book ID: 102991001
Publisher: Elsevier Science
Year: 1982
Tongue: English
Weight: 685 KB
Volume: 110
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(82)85024-6

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✦ Synopsis

Derivatives of methyl 2-amino-2-deoxy-cr-D-altropyranoside-2-1siV and methyl 3-amino-3-deoxy-a-D-glucopyranoside-3-'s~ have been synthesized by addition of phthalimide-15N to methyl 2,3-anhydro-4,6-O-benzylidene-a-D-allopyranoside.

The structures of the phthalimido derivatives that resulted have been proved chemically, by conversion into known aminodeoxy derivatives, and spectroscopically, by 'Hand 13C-n.m.r. spectroscopy. 'H-N.m.r. spectroscopy at 360 MHz also allowed definition of the configurations and conformations of the labeled and unlabeled phthalimido derivatives, and the measurement of vicinal 'H-15N coupling-constants that are characteristic of 'H-l'N dihedral angles of -60".

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