1,6-anhydro-N-acetyl-beta-D-glucosamine in the oligosaccharide syntheses. I. Synthesis of 3-acetate and 3-benzoate of 1,6-anhydro-N-acetyl-beta-D-glucosamine via the 4-O-trityl derivative

Citation
Tv. Tyrtysh et al., 1,6-anhydro-N-acetyl-beta-D-glucosamine in the oligosaccharide syntheses. I. Synthesis of 3-acetate and 3-benzoate of 1,6-anhydro-N-acetyl-beta-D-glucosamine via the 4-O-trityl derivative, BIOORG KHIM, 26(6), 2000, pp. 460-465
Citations number
25
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANICHESKAYA KHIMIYA
ISSN journal
01323423 → ACNP
Volume
26
Issue
6
Year of publication
2000
Pages
460 - 465
Database
ISI
SICI code
0132-3423(200006)26:6<460:1ITOSI>2.0.ZU;2-T
Abstract
3-O-Acetyl and 3-O-benzoyl derivatives of 1,6-anhydro-N-acetyl-beta-D-gluco samine were synthesized via its selective tritylation followed by the 3-O-a cylation and removal of the trityl protective group. Tritylium trifluoromet hanesulfonate, which can easily be prepared by mixing solutions of tripheny lcarbinol and trimethylsilyl trifluoromethanesulfonate in an equimolar rati o, was suggested as a reagent for the effective tritylation of a secondary hydroxyl group.