138298-68-7

Basic information

• Product Name: (2R,3R)-3-((1-cyclohexylethyl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester
• Synonyms: (2R,3R)-3-((1-cyclohexylethyl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester
• CAS NO: 138298-68-7
• Molecular Weight: 288.341
• Mol File: 138298-68-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3-((1-cyclohexylethyl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-((1-cyclohexylethyl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester(138298-68-7)
• EPA Substance Registry System: (2R,3R)-3-((1-cyclohexylethyl)oxy)-2-hydroxy-1,4-butanedioic acid dimethyl ester(138298-68-7)

Safety Data

• Hazardous Substances Data: 138298-68-7(Hazardous Substances Data)

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 114026-66-3 (4R,5R)-2-cyclohexyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 608-68-4 dimethyl L-tartrate 

Downstream Products

• 3113-99-3 (R)-1-cyclohexylethanol 

Relevant articles and documents

Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission

Johnson-type acetals derived from dimethyl tartrate give, after opening with Me2BBr and cuprate displacement, secondary alcohols with high diastereoselectivity (>30:1). The mechanism proposed for the induction of diastereoselectivity is downstream from the ring fission. It implies a direct participation of the Lewis acid as a source of nucleophile and the stereospecific transformation of the resulting bromo acetal through an invertive and temperature-dependent process. The acetals are prepared by reaction of the desired aldehyde with dimethyl tartrate. Removal of the auxiliary is accomplished through Sml2 reduction or by an addition - elimination protocol using methoxide.