370554-15-7

Upstream product

• 370554-12-4 (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 21209-51-8 N-benzyloxycarbonyl-L-serine benzyl ester 
• 370554-14-6 O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester 
• 625388-51-4 (2S,4aR,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 370554-13-5 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 

Downstream Products

• 370554-27-1 O-[2-azido-3,4-di-O-benzyl-6-O-{3',6'-di-O-benzyl-2'-deoxy-2'-(4,5-dichlorophthalimido)-4'-O-(3'',4'',6''-tri-O-benzyl-2''-O-p-toluoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl}-2-deoxy-α-D-galactopyranosyl]-N-(benzyloxycarbonyl)-L-serine benzyl ester 

Relevant academic research and scientific papers

Convergent total syntheses of oligosaccharides by one-pot sequential stereoselective glycosylations

A convergent total synthesis of F1α antigen, a member of the tumor-associated O-linked mucin glycosyl amino acid, was tried by one-pot sequential glycosylation. Highly α-selective glycosylation of amino acid 7 with thioglycoside 6 was successfully carried out by combining trityl trifluoromethanesulfonate (TrOTf) and N-iodosuccimide (NIS) which gave glycosyl amino acid 21 in high yield (97%, α/β = 83/17). Next, the glycosylation of thioglycoside 4 with galactosyl phenyl carbonate 2 or fluoride 3 was tried by the promotion of trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] or trifluoromethanesulfonic acid (TfOH); protected F1α 25 was afforded in 80 or 89% overall yield, respectively, by the further addition of glycosyl amino acid 5 and NIS. The desired trisaccharide was obtained in high yield after removal of the protecting groups. Next, a convergent total synthesis of branched hepta-β-glucoside 30 having phytoalexin-elicitor activity was efficiently performed by way of two one-pot sequential glycosylation reactions: that is, trisaccharide 34 was synthesized in high yield by TfOH-catalyzed one-pot glycosylation using three given monosaccharides (31, 35, and 36) as shown in Scheme 12 and by subsequent selective deprotection of 6′-O-TBDPS group. The second one-pot glycosylation of trisaccharide 34 with three monosaccharides (31, 32, and 33d) also proceeded smoothly to afford heptaglucoside 43 stereoselectively in 48% total yield based on monosaccharide 32. Phytoalexin-elicitor active branched hepta-β-glucoside 30 was afforded by the sequential deprotection.

A convergent total synthesis of the mucin related F1α antigen by one-pot sequential stereoselective glycosylation

A convergent total synthesis of F1α antigen, a member of the tumor-associated O-linked mucin glycosyl amino acids, was accomplished by one-pot sequential glycosylation. In the first step, the corresponding disaccharide was formed from galactosyl phenylcarbonate 2 or fluoride 3 and thioglycoside 4 by the promotion of TrB(C6F5)4 or TfOH, and following glycosylation of glycosyl amino acid 5 by further addition of N-iodosuccinimide(NIS) afforded protected F1α in 80 or 89% overall yield, respectively. By the subsequent deprotection, F1α antigen was obtained in good yield.