152488-28-3

Basic information

• Product Name: phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside
• Synonyms: phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside
• CAS NO: 152488-28-3
• Molecular Weight: 522.576
• Mol File: 152488-28-3.mol

Chemical Properties

• CAS DataBase Reference: phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside(152488-28-3)
• EPA Substance Registry System: phenyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside(152488-28-3)

Safety Data

• Hazardous Substances Data: 152488-28-3(Hazardous Substances Data)

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 152488-27-2 phenyl 2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside 
• 124477-00-5 phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 120095-47-8 phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 548477-85-6 phenyl (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside 
• 849132-40-7 phenyl 4-O-acetyl-2,6-di-O-benzoyl-3-O-phenoxythiocarbonyl-1-thio-β-D-galactoside 
• 849132-44-1 phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside 
• 849132-42-9 phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside 
• 849132-41-8 phenyl 4-O-acetyl-2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-xylo-hexoside 
• 849132-43-0 phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside 
• 535961-73-0 phenyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 

Relevant articles and documents

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

A stereospecific approach towards the synthesis of 2-deoxy α- and β-glycosides based on a 1,2-ethyl (phenyl) thio group migration

Iodonium ion (NIS/TfOH)-assisted glycosylation of a sugar acceptor with properly protected ethyl (phenyl) 2-O-phenoxythiocarbonyl 1-thio-β-D-gluco- or 1-thio-α-D-mannopyranoside donors gives the respective 1,2-trans linked 2'-ethyl (phenyl) thio-2'-deoxy-α-D-manno- or β-D-glucopyranosides.