653575-98-5

Basic information

• Product Name: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside
• Synonyms: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside
• CAS NO: 653575-98-5
• Molecular Weight: 652.593
• Mol File: 653575-98-5.mol

Chemical Properties

• CAS DataBase Reference: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside(653575-98-5)
• EPA Substance Registry System: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-1-thio-α-D-mannopyranoside(653575-98-5)

Safety Data

• Hazardous Substances Data: 653575-98-5(Hazardous Substances Data)

Upstream product

• 653575-97-4 (E)-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfanyl-D-arabino-hex-1-enitol 
• 31238-57-0 diphenyl(phenylthiomethyl)phosphine oxide 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 

Downstream Products

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 84207-52-3 cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside 

Relevant articles and documents

Tuning the stereoelectronic properties of 1-sulfanylhex-1-enitols for the sequential stereoselective synthesis of 2-deoxy-2-iodo-β- d -allopyranosides

The preparation of challenging 2-deoxy-2-iodo-β-d-allo precursors of 2-deoxy-β-d-ribo-hexopyranosyl units and other analogues is reported using a robust olefination-cyclization-glycosylation sequence. Here, we particularly focus on tuning the stereoelectronic properties of the alkenyl sulfides intermediates in order to improve the diastereoselectivity of the cyclization step and, hence, the efficiency of the overall transformation. Phosphine oxides with the general formula Ph2P(O)CH2SR (R = t-Bu, Cy, p-MeOPh, 2,6-di-ClPh, and 2,6-di-MePh) were easily synthesized and subsequently used in the olefination reaction with 2,3,5-tri-O-benzyl-d-ribose and -d-arabinose. The corresponding sugar-derived alkenyl sulfides were submitted to a 6-endo [I+]-induced cyclization, and the resulting 2-deoxy-2-iodohexopyranosyl-1-thioglycosides were used as glycosyl donors for the stereoselective synthesis of 2-deoxy-2-iodohexopyranosyl glycosides. Among the different S-groups studied, t-Bu derivative was the best performer for the synthesis of cholesteryl 2-deoxy-2-iodomannopyranosides, whereas for the synthesis of 2-deoxy-2-iodoallopyranosides none of the derivatives here studied proved superior to the phenyl analogue previously described. Glycosylation of cholesterol with different d-allo and d-manno derivatives produced 2-deoxy-2-iodoglycosides with stereoselectivities in the same order in each case, reinforcing the involvement of an oxocarbenium ion as the common intermediate of this crucial glycosylation step.

Stereoselective synthesis of 2-deoxy-2-iodo-glycosides from furanoses. A new route to 2-deoxy-glycosides and 2-deoxy-oligosaccharides of ribo and xylo configuration

A general procedure for the stereoselective synthesis of 2-deoxy-2-iodo-hexo- and -hepto-pyranosyl glycosides from furanoses is reported. The proposed methodology provides a new route for accessing 2-deoxy-oligosaccharides. The procedure involves three re

Phenyl 2-Deoxy-2-iodo-1-thio-glycosides: New Glycosyl Donors for the Stereo-selective Synthesis of 2-Deoxy-oligosaccharides

Phenyl 2-deoxy-2-iodo-1-thioglycosides, prepared from simple pentoses by olefination and iodine-induced cyclization, have proved to be efficient glycosyl donors for the stereoselective synthesis of 2-deoxy-2-iodo- oligosaccharides, which are precursors of