158419-97-7

Basic information

• Product Name: benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside
• Synonyms: benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS NO: 158419-97-7
• Molecular Weight: 702.782
• Mol File: 158419-97-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside(158419-97-7)
• EPA Substance Registry System: benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside(158419-97-7)

Safety Data

• Hazardous Substances Data: 158419-97-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 70569-27-6 benzyl 1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 158419-88-6 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl thiocyanate 
• 6921-34-2 benzylmagnesium chloride 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 100-39-0 benzyl bromide 
• 247257-17-6 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate 

Downstream Products

• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant articles and documents

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides

Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.