367252-57-1

Basic information

• Product Name: all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester
• Synonyms: all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester
• CAS NO: 367252-57-1
• Molecular Weight: 374.475
• Mol File: 367252-57-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester(367252-57-1)
• EPA Substance Registry System: all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester(367252-57-1)

Safety Data

• Hazardous Substances Data: 367252-57-1(Hazardous Substances Data)

Upstream product

• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 367252-53-7 1,5-dibromo-3-(1-ethylpropoxy)-2,4-dimethoxybenzene 
• 367252-51-5 2-(1-ethylpropoxy)-1,3-dimethoxybenzene 
• 4358-72-9 methanesulfonic acid 1-ethylpropyl ester 
• 367252-55-9 5-(1-ethylpropoxy)-4,6-dimethoxyisophthalic acid diethyl ester 

Downstream Products

• 367252-59-3 all-cis-5-(1-ethylpropoxy)-4,6-dihydroxycyclohexane-1,3-dicarboxylic acid diethyl ester 
• 367252-69-5 (1S,3R,4R,5R,6S)-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid 1-ethyl ester 
• 367252-61-7 (1R,3S,4S,5S,6R)-5-(1-ethylpropoxy)-4,6-dihydroxycyclohexane-1,3-dicarboxylic acid 1-ethyl ester 
• 196618-13-0 oseltamivir 

Relevant articles and documents

New, efficient synthesis of oseltamivir phosphate (Tamiflu) via enzymatic desymmetrization of a meso-1,3-cyclohexanedicarboxylic acid diester

(Chemical Equation Presented) A new, enantioselective synthesis of the influenza neuraminidase inhibitor prodrug oseltamivir phosphate 1 (Tamiflu) and its enantiomer ent-1 starting from cheap, commercially available 2,6-dimethoxyphenol 10 is described. The main features of this approach comprise the cis-hydrogenation of 5-(1-ethyl-propoxy)-4,6-dimethoxy-isophthalic acid diethyl ester (6a) and the desymmetrization of the resultant all-cis meso-diesters 7a and 7b, respectively. Enzymatic hydrolysis of the meso-diester 7b with pig liver esterase afforded the (S)-monoacid 8b, which was converted into cyclohexenol 17 via a Curtius degradation and a base-catalyzed decarboxylative elimination of the Boc-protected oxazolidinone 14. Introduction of the second amino function via SN2 substitution of the corresponding triflate 18 with NaN3 followed by azide reduction, N-acetylation, and Boc-deprotection gave oseltamivir phosphate 1 in a total of 10 steps and an overall yield of ～30%. The enantiomer ent-1 was similarly obtained via an enzymatic desymmetrization of meso-diester 7a with Aspergillus oryzae lipase, providing the (R)-monoacid ent-8a.