77870-90-7

Basic information

• Product Name: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate
• Synonyms: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate
• CAS NO: 77870-90-7
• Molecular Weight: 775.896
• Mol File: 77870-90-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate(77870-90-7)
• EPA Substance Registry System: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propanoate(77870-90-7)

Safety Data

• Hazardous Substances Data: 77870-90-7(Hazardous Substances Data)

Upstream product

• 14464-15-4 methyl 2-(benzyloxycarbonylamino)-3-hydroxypropanoate 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 329365-81-3 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl methanethiosulfonate 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 329365-86-8 ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 82300-58-1 dibezylphosphoryl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 135195-50-5 (S)-2-Benzyloxycarbonylamino-3-trimethylsilanyloxy-propionic acid methyl ester 

Relevant articles and documents

Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation

A versatile glycosylation reaction is used to establish the process of sulfoxide covalent catalysis. Hemiacetals are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, nBu2SO, for coupling with various nucleophiles (Nu; se

AuCl3- and AuCl3-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature. We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.

Glycosyl disulfides: Novel glycosylating reagents with flexible aglycon alteration

Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning strategies.