1206157-70-1

Basic information

• Product Name: O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-α-D-galactopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester
• Synonyms: O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-α-D-galactopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester
• CAS NO: 1206157-70-1
• Molecular Weight: 767.917
• Mol File: 1206157-70-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-α-D-galactopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-α-D-galactopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester(1206157-70-1)
• EPA Substance Registry System: O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-α-D-galactopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester(1206157-70-1)

Safety Data

• Hazardous Substances Data: 1206157-70-1(Hazardous Substances Data)

Upstream product

• 1206157-59-6 1-C-acetyl-3,4,6-tri-O-benzyl-1,2-cyclopropane-1,2-deoxy-α-D-galactopyranose 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 
• 1206157-57-4 3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-talopyranosyl)-propene 
• 1206157-58-5 1-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-talopyranosyl)-acetone 

Relevant articles and documents

Stereoselective synthesis of 2-C-branched (acetylmethyl) oligosaccharides and glycoconjugates: Lewis acid-catalyzed glycosylation from 1,2-cyclopropaneacetylated sugars

1,2-Cyclopropaneacetylated sugars as glycosyl donors reacted with a series of glycosyl acceptors (monosaccharides, amino acids, and other alcohols) in the presence of Lewis acid to produce oligosaccharides and glycoconjugates containing 2-C-acetylmethylsugars. Galactosyl donor gave good to excellent α-selectivities with TMSOTf as a catalyst, whereas galactosyl donor offered moderate to good β-selectivities when BF3·Et 2O was used as a catalyst. However, glucosyl donors produced β-exclusive selectivity under both conditions. The stereoselectivities of glycosylation depend on the reactivity of donor sugars and Lewis acid catalyst, which effectively dictated the glycosylation pathways. The evidence suggests that galactosyl donors (e.g., 7) can undergo SN1 pathway with a strong Lewis acid (TMSOTf) and SN2 pathway under BF 3·Et2O, whereas the glucosyl donors (e.g., 8 and 10) followed SN2 pathway. The stereoselectivity was also consequential to the formation of a C2′-acetal intermediate formed via the 2-C-acetylmethyl group and the anomeric carbonium intermediate in glycosylation.