85951-15-1

Basic information

• Product Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 85951-15-1
• Molecular Weight: 470.497
• Mol File: 85951-15-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate(85951-15-1)
• EPA Substance Registry System: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate(85951-15-1)

Safety Data

• Hazardous Substances Data: 85951-15-1(Hazardous Substances Data)

Upstream product

• 696-63-9 4-Methoxybenzenethiol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 19879-84-6 tetraacetyl thioglucose 
• 696-62-8 para-iodoanisole 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 96158-82-6 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triol 

Relevant articles and documents

Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.

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.

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