146788-06-9

Basic information

• Product Name: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• Synonyms: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS NO: 146788-06-9
• Molecular Weight: 559.567
• Mol File: 146788-06-9.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester(146788-06-9)
• EPA Substance Registry System: (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester(146788-06-9)

Safety Data

• Hazardous Substances Data: 146788-06-9(Hazardous Substances Data)

Upstream product

• 146788-04-7 (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146815-47-6 (2R,3S,4R,5R,6R)-5-Acetylamino-2-fluoro-4-hydroxy-3-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146815-46-5 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-fluoro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 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 
• 75-36-5 acetyl chloride 
• 146788-05-8 (2R,3S,4R,5S,6R)-4-Acetoxy-6-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Total synthesis of GD3, a ganglioside

On the basis of new methodology involving α-stereo-controlled sialylation using our 2-halo-3β-phenylthio-Neu5Ac and construction of Neu5Ac(α2-8)Neu5Ac due to differential reactivity between 2-chloro and 2-fluoro-Neu5Ac, we realized an efficient total synthesis of GD3.

Simple construction of Neu5Ac(α2-8)Neu5Ac and total synthesis of ganglioside GD3

Glycosylation of an 8-unprotected sialyl fluoride 16 with 2β-chloro-3β-phenylthio-Neu5Ac 2 gave the desired α-disialate 23. Subsequent glycosylation of a thiolactoside 19 with the disialyl fluoride 23 gave the tetrasaccharide 28. Synthesis of GD3 1 was realized by condensation of the tetrasaccharide 28 with azidosphingosine 31, following our previously reported GM3 synthesis procedure.