162316-88-3

Upstream product

• 54769-36-7 N-benzoyloxybenzotriazole 
• 162316-87-2 Ethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-α-D-glucopyranoside 
• 151123-93-2 Ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 162316-82-7 Ethyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-α-D-glucopyranoside 
• 162427-46-5 Ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 162316-86-1 Ethyl 2,3-di-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-α-D-glucopyranoside 
• 625388-43-4 ethyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-1-thio-α-D-glucopyranoside 
• 151123-94-3 Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 473545-19-6 ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-D-glucopyranoside 

Downstream Products

• 162316-89-4 Ethyl 2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-3-O-chloroacetyl-1-thio-α-D-glucopyranoside 
• 162317-08-0 8-Methoxycarbonyloctyl O-(2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-O-benzyl-β-D-glucopyranoside 
• 162316-94-1 8-Methoxycarbonyloctyl 2-O-benzoyl-4-O-benzyl-β-D-glucopyranoside 
• 162316-93-0 8-Methoxycarbonyloctyl 2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 
• 162316-92-9 8-Methoxycarbonyloctyl 2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-3-O-chloroacetyl-β-D-glucopyranoside 
• 162317-10-4 8-Methoxycarbonyloctyl O-(2-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-O-benzyl-β-D-glucopyranoside 
• 162317-09-1 8-Methoxycarbonyloctyl O-(2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-O-benzyl-β-D-glucopyranoside 

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.

SYNTHESIS OF 8-METHOXYCARBONYLOCTYL β-GLYCOSIDES OF TRI- AND TETRASACCHARIDES RELATED TO SCHIZOPHYLLAN AND NEOGLYCOPROTEINS THEREFROM

The 8-methoxycarbonyloctyl β-glycosides of the trisaccharides O-β-D-Glcp-(1->6)-O-β-D-Glcp-(1->3)-D-Glcp and O-β-D-Glcp-(1->3)-O-6)>-D-Glcp and of the tetrasaccharide O-β-D-Glcp-(1->3)-O-6)>-O-β-D-Glcp-(1->3)-D-Glcp, correspond