Efficient syntheses of methyl 2-amino-2-deoxy-3,4,6-tri-O-benzyl-alpha-D-glucopyranoside and its 2-tert-butoxycarbonylamino- and 2-methylamino derivatives from N-acetyl-D-glucosamine

Citation
C. Henry et al., Efficient syntheses of methyl 2-amino-2-deoxy-3,4,6-tri-O-benzyl-alpha-D-glucopyranoside and its 2-tert-butoxycarbonylamino- and 2-methylamino derivatives from N-acetyl-D-glucosamine, J CARB CHEM, 18(6), 1999, pp. 689-695
Citations number
17
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
18
Issue
6
Year of publication
1999
Pages
689 - 695
Database
ISI
SICI code
0732-8303(1999)18:6<689:ESOM2>2.0.ZU;2-#
Abstract
The synthesis of the title compounds started with N-acetylglucosamine which was converted into the corresponding methyl glycoside and O-protected with benzyl groups. Subsequent N-protection as its N-BOC-N-acetyl derivative an d sequential removal of the N-acetyl group and of the BOC group led in good yield to the target compounds in multigram amounts.