553663-00-6

Basic information

• Product Name: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside
• Synonyms: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS NO: 553663-00-6
• Molecular Weight: 830.805
• Mol File: 553663-00-6.mol

Chemical Properties

• CAS DataBase Reference: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside(553663-00-6)
• EPA Substance Registry System: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside(553663-00-6)

Safety Data

• Hazardous Substances Data: 553663-00-6(Hazardous Substances Data)

Upstream product

• 177748-62-8 2-(2-iodophenyl)-1-ethanethiol 

Downstream Products

• 553663-10-8 methyl 2,3,6-tri-O-benzyl-4-O-{2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranosyl}-α-D-glucopyranoside 
• 553663-12-0 1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside 
• 553663-09-5 methyl 2,3-di-O-isopropylidene-4-O-{2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranosyl}-α-L-rhamnopyranoside 

Relevant articles and documents

Benzylidene acetal fragmentation route to 6-deoxy sugars: Direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of β-D-rhamnosides from D-mannosyl glycosyl donors

An approach to the stereocontrolled synthesis of β-D-rhamnopyranosides is described in which 2,3-O-benzyl or related 4,6-O-[α-(2-(2-iodophenyl) ethylthiocarbonyl)benzylidene]-mannosyl thioglycosides are first used to introduce the β-D-mannopyranoside link

The 4,6-O-[α-(2-(2-lodophenyl)ethylthiocarbonyl)benzylidene] protecting group: Stereoselective glycosylation, reductive radical fragmentation, and synthesis of β-D-rhamnopyranosides and other deoxy sugars

(Matrix presented) In the thioglycoside/BSP/Tf2O glycosylation method, the 4,6-O-[α-(2-(2-iodophenyl)ethylthiocarbonyl)benzylidene] group enforces β-selectivity in mannopyranosylations. Following glycosylation, treatment with Bu3SnH