A novel synthesis of beta-D-mannopyranosyl azide by phase transfer catalysis.
A simple stereoselective synthesis of per-O-benzoyl-beta-d-mannopyranosyl azide from per-O-benzoyl-alpha-d-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated alpha- and beta-d-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected beta-d-mannopyranosyl azide was prepared by debenzoylation with sodium methoxide in methanol.
Abronina
Polina I
PI
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prospect, 47, 119991 Moscow, Russian Federation.
Kachala
Vadim V
VV
Kononov
Leonid O
LO
D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001386:Azides; D006027:Glycosides; D008358:Mannose