496924-01-7

Basic information

• Product Name: benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside
• Synonyms: benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside
• CAS NO: 496924-01-7
• Molecular Weight: 395.409
• Mol File: 496924-01-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside(496924-01-7)
• EPA Substance Registry System: benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside(496924-01-7)

Safety Data

• Hazardous Substances Data: 496924-01-7(Hazardous Substances Data)

Upstream product

• 102735-44-4 benzyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 100-51-6 benzyl alcohol 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

Syntheses of N-aryl-protected glucosamines and their stereoselectivity in chemical glycosylations

N-Aryl-protecting groups were introduced in glucosamines to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β selectivity. This stereoselectivity seemed to be derived from the formation of an aziridine intermediate. The DMP-protecting group can be removed immediately by using ammonium hexanitratocerate (IV).