66963-55-1

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 
• 1219934-61-8 C₄₇H₄₆O₈ 
• 848047-83-6 (S)-2-((benzyloxycarbonyl)amino)succinic acid 1-allyl ester 4-amide 
• 26061-17-6 N-(benzyloxycarbonyl)-L-asparaginyl-L-valine tert-butyl ester 
• 98-88-4 benzoyl chloride 
• 148926-02-7 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 66963-53-9 1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose 
• 1350618-88-0 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-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).

Gold(I)-Catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors: General scope and application in the synthesis of a cyclic triterpene saponin

Glycosyl ortho-alkynylbenzoates have emerged as a new generation of donors for glycosidation under the catalysis of gold(I) complexes such as Ph 3PAuOTf and Ph3PAuNTf2 (Tf= trifluoromethanesulfonate). A wide variety of these donors, including 2-deoxy sugar and sialyl donors, are easily prepared and shelf stable. The glycosidic coupling yields with alcohols are gener-ally excellent; even direct coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α-selective glycosylation with a 2-deoxy sugar donor and β-selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective glycosylation of the carboxylic acid and a new one-pot sequential glycosylation sequence have been implemented.

Facile preparation of 1,6-anhydrohexoses using solvent effects and a catalytic amount of a Lewis acid.

Refluxing solutions of monosaccharides, unprotected at the 6-position and carrying O-methyl, S-ethyl, O-acetyl and OH-groups at the anomeric center, in acetonitrile containing a catalytic amount of a Lewis acid (O.1-0.4 equiv.) yielded 1,6-anhydrohexopyra

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.