1042397-90-9

Upstream product

• 498-07-7 levoglucosan 
• 100-39-0 benzyl bromide 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 1393083-67-4 6-O-acetyl-2,3,4,2′,3′,4′,6′-hepta-O-benzyl-1-thio-α,α-D-trehalose 
• 130539-62-7 6-O-acetyl-1-S-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-α-D-glucopyranose 
• 1452840-23-1 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranosyl-(1,1’)-dithio-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 1452840-20-8 bis-(2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranosyl)-1,1'-disulfide 
• 126461-56-1 benzyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 1330066-30-2 C₆₃H₆₆O₁₁S 
• 1330066-29-9 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranose 

Relevant academic research and scientific papers

One-pot, highly stereoselective synthesis of dithioacetal-α,α-diglycosides

A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.

Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars

Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).

Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS

The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.

A direct and stereospecific approach to the synthesis of α-glycosyl thiols

A new simple method for the synthesis of α-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded α-glycosyl thiols in very high yields and in a stereospecific way. The Royal Society of Chemistry 2008.