176449-83-5

Basic information

• Product Name: 2,2-Dimethyl-propionic acid (2S,3S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-4-oxo-5-phenoxythiocarbonyloxy-tetrahydro-pyran-3-yl ester
• Synonyms: 2,2-Dimethyl-propionic acid (2S,3S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-4-oxo-5-phenoxythiocarbonyloxy-tetrahydro-pyran-3-yl ester
• CAS NO: 176449-83-5
• Molecular Weight: 496.579
• Mol File: 176449-83-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,2-Dimethyl-propionic acid (2S,3S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-4-oxo-5-phenoxythiocarbonyloxy-tetrahydro-pyran-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-propionic acid (2S,3S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-4-oxo-5-phenoxythiocarbonyloxy-tetrahydro-pyran-3-yl ester(176449-83-5)
• EPA Substance Registry System: 2,2-Dimethyl-propionic acid (2S,3S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-2-methoxy-4-oxo-5-phenoxythiocarbonyloxy-tetrahydro-pyran-3-yl ester(176449-83-5)

Safety Data

• Hazardous Substances Data: 176449-83-5(Hazardous Substances Data)

Upstream product

• 76520-84-8 methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside 
• 90213-79-9 (2S,3S,5R,6R)-5-hydroxy-2-methoxy-4-oxo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl pivalate 
• 1005-56-7 phenylcarbonochloridothioate 

Relevant articles and documents

Deoxygenation at C-4 and stereospecific branched-chain construction at C-3 of a methyl hexopyranuloside. Synthetic approach to the amipurimycin sugar moiety

A five-step synthesis from 3 leading to a partially protected amipurimycin sugar moiety 14 in an overall yield of 47% is described and includes deoxygenation at C-4 and regio- and stereoselective construction of the branched chain. Deoxygenation at C-4 of 3 was possible by three different methods. Radical reduction with tri-n-butyltin hydride of the appropriate phenoxythiocarbonyl derivative afforded the desired deoxysugar 5 in 47% overall yield together with the secondary products 6 and 7 due to depivaloylation at C-2 and elimination of methanol. The most adequate deoxygenation procedure used the system Ph3P/I2/imidazole which led to the preparation of 5 in one step in 61% yield. When the system Ph3PBr2/Ph3P was tried, only 8 was formed due to elimination of methanol. The synthesis of 5 was then accomplished by reaction of 8 with methanol in the presence of triphenylphosphine hydrobromide in 37% overall yield. Branched-chain construction was accomplished by Wittig reaction of 5 with [(ethoxycarbonyl)methylene]triphenylphosphorane, followed by osmilation and reduction with lithium aluminum hydride. Isopropylidenation of 14 afforded 16 with a free hydroxy group at C-6 for chain elongation and further synthesis of amipurimycin.