66963-53-9

Upstream product

• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 66963-55-1 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose 

Downstream Products

• 1350618-71-1 1,6-anhydro-3,4-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranose 
• 54503-52-5 C₂₂H₂₄O₆ 
• 1350618-73-3 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose 
• 1350618-79-9 3,4-di-O-benzyl-1-thio-α-D-glucopyranose 
• 1350618-87-9 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-D-glucopyranose 
• 1350618-88-0 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-D-glucopyranose 
• 1350618-89-1 3,4-di-O-benzyl-2-O-pivaloyl-1-thio-α-D-glucopyranose 
• 1350618-93-7 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-1-thio-α-D-glucopyranose 
• 1610840-25-9 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→2)-1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose 
• 1610840-24-8 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→2)-1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose 

Relevant academic research and scientific papers

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).

Regioselective De-O-benzylation with Lewis Acids

Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.

Anhydro-sugars

The invention relates to novel 1,6-anhydro-β-D-hexopyranose derivatives of the formula I STR1 in which R2 is hydrogen, methyl or aromatic acyl, R3 and R4 are alkyl, alkenyl or aralkyl and one of the radicals R3