1035895-88-5

Basic information

• Product Name: (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester
• Synonyms: (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester
• CAS NO: 1035895-88-5
• Molecular Weight: 312.409
• Mol File: 1035895-88-5.mol

Chemical Properties

• CAS DataBase Reference: (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester(1035895-88-5)
• EPA Substance Registry System: (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester(1035895-88-5)

Safety Data

• Hazardous Substances Data: 1035895-88-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester is used as a building block for the development of new pharmaceutical compounds due to its unique structure and functional groups. The presence of amino, acetylamino, and ethyl ester groups can be exploited for the synthesis of various drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester can be utilized as an intermediate or a key component in the synthesis of more complex organic molecules. Its versatile structure allows for further functionalization and modification, making it a valuable asset in the development of novel organic compounds.
Used in Chemical Research:
(3S,4S,5R)-4-acetylamino-5-amino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester can also be employed in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its unique structure and functional groups can provide insights into the reactivity and selectivity of different chemical transformations, contributing to the advancement of chemical knowledge and innovation.

Upstream product

• 204254-98-8 C₁₄H₂₃N₃O₄ 

Relevant articles and documents

Preparation method of oseltamivir enantiomer

The invention relates to a preparation method of an oseltamivir enantiomer as shown in a formula I. The method includes the steps: attacking epoxy from back surface by a compound II through sodium azide under the action of ammonium chloride to obtain a compound III; catalyzing the compound III to obtain a compound IV; treating the compound IV under the actions of triethyl silicane and titanium tetrachloride to obtain a compound V; reducing azide by the compound V under the action of triphenylphosphine, and performing loop closing on the compound V and adjacent hydroxyls to obtain a compound VI; attacking cyclamine to open rings from back surface by the compound VI through sodium azide under the action of ammonium chloride, simultaneously overturning a configuration, and performing acetylation by the aid of acetic anhydride to obtain a compound VII; performing Staudinger reaction on the compound VII under the action of triphenylphosphine to reduce the azide into amino to obtain the oseltamivir enantiomer as shown in the formula I. The preparation method of the oseltamivir enantiomer has significance for quality research and quality control of oseltamivir phosphate.

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.