154172-26-6

Basic information

• Product Name: allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside
• CAS NO: 154172-26-6
• Molecular Weight: 531.649
• Mol File: 154172-26-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside(154172-26-6)
• EPA Substance Registry System: allyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside(154172-26-6)

Safety Data

• Hazardous Substances Data: 154172-26-6(Hazardous Substances Data)

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 168037-65-8 (E)-2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose oxime 
• 154125-84-5 (2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosylidene)amino 4-methylbenzene-1-sulfonate 
• 154125-89-0 2-acetamido-1,5-anhydro-1-azi-3,4,6-tri-O-benzyl-2-deoxy-D-glucitol 
• 154125-83-4 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-gluconhydroximo-1,5-lactone 
• 154125-85-6 2-acetamido-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-hydrazi-D-glucitol 
• 182618-39-9 (S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester 
• 182618-48-0 (S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 
• 182618-25-3 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid 
• 65729-90-0 1-chloro-N-acetyl-3,4,6-tri-O-benzyl-α-D-glucosamine 
• 34051-37-1 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton 
• 4171-79-3 N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide 

Relevant articles and documents

127. C-glycoside analogues of N4-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine: synthesis and conformational analysis of a cyclic C-glycopeptide

The synthesis of C-glycosidic analogues 15-22 of N4-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine (ASn(N4GlcNAc)) possessing a reversed amide bond as an isosteric replacement of the N-glycosidic linkage is presented. The peptide cyclo(-D-Pro-Phe-Ala-CGaa-Phe-Phe-) (CGaa = C-glycosylated amino acid; 24) was prepared to demonstrate that 3-[(3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D- guloheptonoyl)amino]-2-[(9H-fluoren-9-yloxycarbonyl)amino]propanoic acid (22) can be used in solid-phase peptide synthesis. The conformation of 24 was determined by NMR and molecular-dynamics (MD) techniques. Evidence is provided that the CGaa side chain interacts with the peptide backbone. The different C-glycosylated amino acids 15-21 were prepared by coupling 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo- heptonic acid (4) with diamino-acid derivatives 8-14 in 83-96% yield. The synthesis of 4 was performed from 2-(acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)tributylstannane (2) by treatment with BuLi and CO2 in 83% yield. Similarly, propyl isocyanat yielded the glycoheptonamide 7 in 52% from 2. Compound 2 was obtained from 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose (1) by chlorination and addition of tributyltinlithium in 74% yield. A procedure for a multigram-scale synthesis of 1 is given.