426206-55-5

Basic information

• Product Name: {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane]
• Synonyms: {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane]
• CAS NO: 426206-55-5
• Molecular Weight: 377.115
• Mol File: 426206-55-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane](CAS DataBase Reference)
• NIST Chemistry Reference: {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane](426206-55-5)
• EPA Substance Registry System: {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane](426206-55-5)

Safety Data

• Hazardous Substances Data: 426206-55-5(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 176166-15-7 cis-(1S,2S)-1,2-dihydroxy-3-chlorocyclohex-3-ene 
• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1392229-29-6 (4S,5S)-3-chloro-4,5-dihydroxycyclohex-2-enone 
• 1392229-39-8 (4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-3-chlorocyclohex-2-en-1-one 

Relevant articles and documents

A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A.

An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.

A chemoenzymatic synthesis of the 12-membered macrolide (-)-cladospolide A

The enantiomerically pure cis-1,2-dihydrocatechol 7, which is obtained by microbial oxidation of chlorobenzene, has been converted, via a sequence of reactions including ring-closing metathesis and Yamaguchi lactonisation steps, into the natural product (-)-cladospolide A (1).