27526-42-7

Basic information

• Product Name: phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside
• Synonyms: phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside
• CAS NO: 27526-42-7
• Molecular Weight: 439.486
• Mol File: 27526-42-7.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside(27526-42-7)
• EPA Substance Registry System: phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside(27526-42-7)

Safety Data

• Hazardous Substances Data: 27526-42-7(Hazardous Substances Data)

Upstream product

• 51450-09-0 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 882-33-7 diphenyldisulfane 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 4551-15-9 phenylthiotrimethylsilane 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 108-98-5 thiophenol 

Downstream Products

• 1258391-59-1 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside phenyl (R,S)-sulfoxide 
• 173725-22-9 n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 129729-51-7 methyl 2,3,4-tri-O-benzyl-6-O-(3’,4’,6’-tri-O-acetyl-2’-N-acetyl-2’-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 371123-32-9 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester 
• 371123-21-6 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(acetyl-tert-butoxycarbonyl-amino)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 
• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 128960-84-9 N-((3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2Hpyran-3-yl)acetamide 

Relevant articles and documents

Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature

A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.

Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.

Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine

The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline.