195193-39-6

Basic information

• Product Name: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• Synonyms: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS NO: 195193-39-6
• Molecular Weight: 629.706
• Mol File: 195193-39-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(195193-39-6)
• EPA Substance Registry System: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(195193-39-6)

Safety Data

• Hazardous Substances Data: 195193-39-6(Hazardous Substances Data)

Upstream product

• 120104-58-7 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 5188-07-8 sodium thiomethoxide 

Relevant articles and documents

Studies on α-sialylation using sialyl donors with an auxiliary 3-thiophenyl group

Reaction of the methyl ester of 2-chloro-3-S-phenyl-3-thiosialic acid (4) with sodium thiomethoxide in acetonitrile at 0°C affords the methyl ester of 2-S-methyl-3-S-phenyl-2,3-dithio-α-sialic acid (6a) in quantitative yield. Sialylation of tetrahydropyran-2-methanol (7) and 2-(trimethylsilyl)ethyl 2,2',3,6,6'-penta-O-benzyl-α-lactoside (8) with 6a in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40°C gives α-sialosides 9 and 10 in good yield and excellent stereoselectivity. No β-sialosides are formed in either case. Acetylation of product 10, and the subsequent reductive removal of the 3-thiophenyl group using Ph3SnH, affords 12 - protected GM3 trisaccharide - in 82% yield after two steps. Sialylation of acceptor 8 with chloride 4 using silver triflate as promotor afforded 10 in 48% yield after two days at -15°C in THF. A possible mechanism of sialylation with 6a that involves intermediate α- and β-nitrilium ions is discussed.