797758-75-9

Basic information

• Product Name: (2R,4S,5R,6E,8R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8-trimethylundec-6-en-3-one
• Synonyms: (2R,4S,5R,6E,8R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8-trimethylundec-6-en-3-one
• CAS NO: 797758-75-9
• Molecular Weight: 460.729
• Mol File: 797758-75-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4S,5R,6E,8R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8-trimethylundec-6-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S,5R,6E,8R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8-trimethylundec-6-en-3-one(797758-75-9)
• EPA Substance Registry System: (2R,4S,5R,6E,8R)-2-benzoyloxy-5-(tert-butyldimethylsilyloxy)-4,6,8-trimethylundec-6-en-3-one(797758-75-9)

Safety Data

• Hazardous Substances Data: 797758-75-9(Hazardous Substances Data)

Upstream product

• 155851-20-0 (4R)-3-(1-oxopentyl)-4-phenylmethyloxazolidin-2-one 
• 53531-14-9 (R)-(+)-2-methylpentanal 
• 105-30-6 (R)-2-methylpentan-1-ol 
• 105311-40-8 (R,E)-ethyl 2,4-dimethylhept-2-enoate 
• 797758-73-7 (R,E)-2,4-dimethylhept-2-en-1-ol 
• 105311-41-9 (2E,4R)-2,4-dimethylheptenal 
• 638-29-9 n-valeryl chloride 
• 797758-72-6 (2R,4S,5R,6E,8R)-2-benzoyloxy-5-hydroxy-4,6,8-trimethylundec-6-en-3-one 
• 69739-34-0 t-butyldimethylsiyl triflate 

Relevant articles and documents

Total synthesis of a hemiacetal polypropionate from Siphonaria australis

A highly stereocontrolled synthesis of (2S,3R,5R,6S)-6-[(1E,3R)-1,3- dimethylhex-1-enyl]-2-ethyl-2-hydroxy-3,5-dimethyltetrahydro-4H-pyran-4-one has been achieved in 13 steps and an overall yield of 7.6% from (A)-(+)-4- benzyloxazolidin-2-one. This substrate-controlled asymmetric synthesis utilized Paterson's lactate-derived chiral ketone (2S)-2-(benzoyloxy) pentan-3-one to generate the 5R and 6S stereocentres and alkylation of an Evans' auxiliary to generate the remote side-chain 3R stereocentre. Furthermore, a novel, highly efficient, and selective strategy was used to generate an enol trimethylsilyl ether whose subsequent Mukaiyama aldol condensation gave the acyclic precursor to the final product. A thermodynamically controlled cyclization then gave (2S,3R,5R,6S)-6-[(1E,3R)-1,3-dimethylhex-1-enyl]-2-ethyl-2-hydroxy-3, 5-dimethyltetrahydro-4H-pyran-4-one with control of the 2S and 3R stereocentres. The NMR spectroscopic data and optical rotation obtained for synthetic (2S,3R,5R,6S)-6-[(1E,3R)-1,3-dimethylhex-1-enyl]-2-ethyl-2-hydroxy-3, 5-dimethyltetrahydro-4H-pyran-4-one were consistent with those reported forthe hemiacetal isolated from Siphonaria australis, and thus, prove the absolute and relative configuration of the natural product.