857419-75-1

Upstream product

• 780767-31-9 2-C-(3,4,6-tri-O-benzyl-2-O-tosyl-α-D-mannopyranosyl)acetaldehyde 
• 857419-61-5 3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-propene 
• 767340-70-5 1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene 
• 857419-66-0 3-C-(3',4',6'-tri-O-benzyl-2'-O-tosyl-α-D-mannopyranosyl)-acetone 

Downstream Products

• 1201897-28-0 methyl 2,3,4-tri-O-benzyl-6-O-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 1201897-32-6 1,2;3,4-di-O-isopropylidene-6-thio-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 121654-15-7 (3β)-cholest-5-en-3-yl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 1201897-34-8 O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-β-D-glucopyranosyl)-N-benzyloxycarbonyl-L-threonine methyl ester 
• 1201897-30-4 O-(3,4,6-tri-O-benzyl-2-C-acetylmethyl-2-deoxy-β-D-glucopyranosyl)-N-[(tert-butoxy)carbonyl]-L-serine benzyl ester 
• 1264738-08-0 methyl 2,3-isopropylidene-4-O-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-galactopyranosyl)-α-L-rhamnopyranoside 
• 1201897-27-9 1,2;3,4-di-O-isopropylidene-6-O-(3',4',6'-tri-O-benzyl-2'-C-acetylmethyl-2'-deoxy-β-D-galactopyranosyl)-α-D-galactopyranoside 
• 1581231-48-2 (2R,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-cyclopropyl-2-methyl-hexahydrofuro[2,3-b]pyran 
• 1581231-47-1 (2R,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-ethyl-2-methylhexahydrofuro[2,3-b]pyran 
• 1581231-46-0 (3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2,2-di-methylhexahydrofuro[2,3-b]pyran 
• 1581231-45-9 (2S,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(4-bromophenyl)hexahydrofuro[2,3-b]pyran 
• 1581231-44-8 (2S,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(4-chlorophenyl)hexahydrofuro[2,3-b]pyran 
• 1581231-43-7 (2S,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-(4-tolyl)-hexahydrofuro[2,3-b]pyran 
• 1581231-42-6 (2S,3S,3aR,4R,5S,6R,7aS)-3-acetyl-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methyl-2-phenylhexahydrofuro[2,3-b]pyran 

Relevant academic research and scientific papers

2-C-branched glycosides from 2′-carbonylalkyl 2-O-Ms(Ts)-C- glycosides. A tandem SN2-SN2 reaction via 1,2-cyclopropanated sugars

(Chemical Equation Presented) Under basic conditions, 2′-aldehydo (acetonyl) 2-O-Ms(Ts)-α-C-glycosides undergo an intramolecular S N2 reaction to form 1,2-cyclopropanated sugars, which react with nucleophiles (alcohols, thiols, and azide) at the anomeric carbon to give 2-C-branched glycosides. By way of contrast, the 1,2-cyclopropanes derived from 2′-ketones only react with thiols to give 2-C-branched thioglycosides.

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.

1,2-Migration of 2′-oxoalkyl group and concomitant synthesis of 2-C-branched O-, S-glycosides and glycosyl azides via 1,2-cyclopropanated sugars

Treatment of 2′-oxoalkyl 2-O-Ms(Ts)-α-C-mannosides (4, 5, and 6) with base resulted in 1,2-cyclopropanation via an intramolecular S N2 reaction due to their 1,2-trans-diaxial configurations. The 1,2-cyclopropanated sugars (10 and 13) were react