155814-72-5

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 7473-36-1 (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 

Downstream Products

• 473545-24-3 ethyl 2,3,4-tri-O-benzoyl-1-thio-α-D-glucopyranoside 
• 473545-25-4 ethyl 2,3,4-tri-O-p-chlorobenzoyl-1-thio-α-D-glucopyranoside 
• 473545-26-5 ethyl 1-thio-2,3,4-tri-O-p-(trifluoromethyl)benzoyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Dispiroketals in Synthesis (Part 7): Protection of D-Glucopyranose Substrates.

The formation of 1,8,13,16-tetraoxadispirohexadecanes (dispiroketals) of various D-glucopyranosyl substrates is described.

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.