4358-72-9

Usage

InChI:InChI=1/C6H14O3S/c1-4-6(5-2)9-10(3,7)8/h6H,4-5H2,1-3H3

Upstream product

• 584-02-1 2-pentanol 
• 124-63-0 methanesulfonyl chloride 
• 949908-55-8 pentan-3-yl 2,2,2-trichloroacetimidate 
• 75-75-2 methanesulfonic acid 

Downstream Products

• 24254-57-7 1-ethyl-propyl hydroperoxide 
• 2719-52-0 2-phenylpentane 
• 1196-58-3 (1-ethylpropyl)benzene 
• 367252-51-5 2-(1-ethylpropoxy)-1,3-dimethoxybenzene 
• 6137-03-7 3-ethyl-2-pentanone 
• 488705-88-0 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-7-(3-pentyl)-3,7-dihydro-1H-purine-2,6-dione 
• 617-80-1 2-ethyl-butyronitrile 
• 367252-59-3 all-cis-5-(1-ethylpropoxy)-4,6-dihydroxycyclohexane-1,3-dicarboxylic acid diethyl ester 
• 367252-57-1 all-cis-5-(1-ethylpropoxy)-4,6-dimethoxycyclohexane-1,3-dicarboxylic acid diethyl ester 
• 367252-55-9 5-(1-ethylpropoxy)-4,6-dimethoxyisophthalic acid diethyl ester 
• 367252-61-7 (1R,3S,4S,5S,6R)-5-(1-ethylpropoxy)-4,6-dihydroxycyclohexane-1,3-dicarboxylic acid 1-ethyl ester 
• 367252-53-7 1,5-dibromo-3-(1-ethylpropoxy)-2,4-dimethoxybenzene 
• 196618-13-0 oseltamivir 
• 488705-89-1 4-[(2,4-dichlorophenyl)amino]-2-ethyl-N-methyl-1-(3-pentyl)-1H-imidazole-5-carboxamide 

Relevant academic research and scientific papers

Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation

We herein report a gram-scale, enantioselective synthesis of Tamiflu, in which the key trans-diamino moiety has been efficiently installed via an iron-catalyzed stereoselective olefin diazidation. This significantly improved, iron-catalyzed method is uniquely effective for highly functionalized yet electronically deactivated substrates that have been previously problematic. Preliminary catalyst structure-reactivity-stereoselectivity relationship studies revealed that both the iron catalyst and the complex substrate cooperatively modulate the stereoselectivity for diazidation. Safety assessment using both differential scanning calorimetry (DSC) and the drop weight test (DWT) has also demonstrated the feasibility of carrying out this iron-catalyzed olefin diazidation for large-scale Tamiflu synthesis.

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.

Stereo-specific synthesis of shimikic acid derivatives with improved efficiency

The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula 1starting from an isophthalic acid derivative of formula 24,5-Diamino shikimic acid derivatives are potent inhibitors of viral neuraminidase.