36874-87-0

Basic information

• Product Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-chlorophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-chlorophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 36874-87-0
• Molecular Weight: 474.916
• Mol File: 36874-87-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-chlorophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-chlorophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate(36874-87-0)
• EPA Substance Registry System: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-chlorophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate(36874-87-0)

Safety Data

• Hazardous Substances Data: 36874-87-0(Hazardous Substances Data)

Upstream product

• 106-39-8 bromochlorobenzene 
• 19879-84-6 tetraacetyl thioglucose 
• 637-87-6 1-Chloro-4-iodobenzene 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 106-54-7 p-Chlorothiophenol 
• 604-68-2 α-D-glucopyranose peracetylate 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 

Downstream Products

• 439-03-2 2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 28217-44-9 p-chlorophenyl 1-thio-β-D-glucoside 

Relevant articles and documents

Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides

Here we report a simple route towards the synthesis of thioglycosides, in which electrochemical cross-coupling is used to form a S-C glycosidic bond from protected and unprotected thiosugars with functionalized aryl bromides under base free conditions. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly complex glycosides under mild conditions.

Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars

A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.

InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides

InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t