65058-34-6

Basic information

• Product Name: .alpha.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate
• Synonyms: .alpha.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate
• CAS NO: 65058-34-6
• Molecular Formula: C₂₈H₃₈O₁₈S
• Molecular Weight: 694.66
• Mol File: 65058-34-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 681.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• CAS DataBase Reference: .alpha.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate(65058-34-6)
• EPA Substance Registry System: .alpha.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate(65058-34-6)

Safety Data

• Hazardous Substances Data: 65058-34-6(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 19879-84-6 tetraacetyl thioglucose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 17317-98-5 1-thio-α,α-trehalose 

Downstream Products

• 17317-98-5 1-thio-α,α-trehalose 

Relevant articles and documents

Direct, stereoselective thioglycosylation enabled by an organophotoredox radical strategy

While strategies involving a 2e- transfer pathway have dictated glycosylation development, the direct glycosylation of readily accessible glycosyl donors as radical precursors is particularly appealing because of high radical anomeric selectivity and atom- and step-economy. However, the development of the radical process has been challenging owing to notorious competing reduction, elimination and/or SN side reactions of commonly used, labile glycosyl donors. Here we introduce an organophotocatalytic strategy through which glycosyl bromides can be efficiently converted into corresponding anomeric radicals by photoredox mediated HAT catalysis without a transition metal or a directing group and achieve highly anomeric selectivity. The power of this platform has been demonstrated by the mild reaction conditions enabling the synthesis of challenging α-1,2-cis-thioglycosides, the tolerance of various functional groups and the broad substrate scope for both common pentoses and hexoses. Furthermore, this general approach is compatible with both sp2 and sp3 sulfur electrophiles and late-stage glycodiversification for a total of 50 substrates probed.

Stereoselective synthesis of β-glycosyl thiols and their synthetic applications

A significantly fast reaction condition for the exclusive preparation β-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.

A facile preparation of trehalose analogues: 1,1-thiodisaccharides

The synthesis of 1,1-thiodisaccharide trehalose analogues in good to excellent yields by a Lewis acid (BF3·Et2O)-catalysed coupling of sugar per-O-acetate with thiosugar is described. The reactivity of different sugar per-O-acetates and thiosugars is explored.