101769-63-5

Basic information

• Product Name: ShikiMic Acid Ethyl Ester
• Synonyms: ShikiMic Acid Ethyl Ester;[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester;Ethyl shikimate;ZZJSUXLVNPETPK-BWZBUEFSSA-N
• CAS NO: 101769-63-5
• Molecular Formula: C₉H₁₄O₅
• Molecular Weight: 202.20446
• Mol File: 101769-63-5.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ShikiMic Acid Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: ShikiMic Acid Ethyl Ester(101769-63-5)
• EPA Substance Registry System: ShikiMic Acid Ethyl Ester(101769-63-5)

Safety Data

• Hazardous Substances Data: 101769-63-5(Hazardous Substances Data)

Usage

Uses

Shikimic Acid Ethyl Ester is an intermediate used to synthesize (1S, 5R, 6S)-5-(1-n-Propylethoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester, an analog of (1R,5S,6S)-rel-5-(1-Ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Methyl Ester (E925665) which is an intermediate in the synthesis of neuraminidase inhibitors.

Upstream product

• 138-59-0 shikimic acid 
• 1446467-05-5 C₁₄H₂₀O₆ 
• 1446467-12-4 C₁₃H₁₈O₇ 
• 1446467-11-3 C₁₄H₁₇F₃O₉S 
• 1446467-10-2 C₁₃H₁₈O₇ 
• 1446467-09-9 C₁₁H₁₄O₇S 
• 1446467-08-8 ethyl (3S,4S,5R)-5-acetoxy-3,4-dihydroxycyclohex-1-enecarboxylate 
• 136994-78-0 ethyl (3aR,7R,7aS)-2,2-dimethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 64-17-5 ethanol 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 1132659-99-4 (3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1365542-98-8 (3R,4S,5R)-ethyl 4-hydroxy-5-(methoxymethoxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 204255-06-1 oseltamivir 
• 204255-11-8 oseltamivir phosphate 
• 943515-58-0 (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 204254-92-2 ethyl (3R,4R,5R)-3-(1-ethyl-propoxy)-4-hydroxy-5-methanesulfonyloxycyclohex-1-ene-1-carboxylate 
• 204254-84-2 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 136994-78-0 ethyl (3aR,7R,7aS)-2,2-dimethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate 
• 1217834-81-5 ethyl (1β,5α,6β)-5-(1-ethylpropoxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 

Relevant articles and documents

From plant to drug: Ionic liquids for the reactive dissolution of biomass

We present an ionic liquid (IL) strategy for the reactive dissolution of star anise seeds using different Bronsted-acidic ionic liquids as the solvent and reaction media towards the isolation of important pharmaceutical intermediates; this procedure provi

Industrial synthesis of the key precursor in the synthesis of the anti-influenza drug oseltamivir phosphate (Ro 64-0796/002, GS-4104-02): Ethyl (3R,4S,5S)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1 -ene-1 -carboxylate

Starting from (-)-quinic acid, the title compound was synthesized in seven chemical steps and an overall yield of 35-38%. The route of the improved Gilead synthesis was not changed. However, significant improvements in each step led to a doubled overall yield, a 30% reduction in the number of unit operations, and an excellent quality (≥99%) of the resulting epoxide. A highly regioselective method for the dehydration of a quinic acid to a shikimic acid derivative and for the reduction of a cyclic ketal was found. Alternatively, the title compound was synthesized in six chemical steps and 63-65% yield from commercially available (-)-shikimic acid. Compared to the optimized quinic acid route, the production time was reduced by about 50%. The quality of epoxide produced from either natural product was equivalent. Therefore (-)-shikimic acid is the preferred raw material. The absolute configuration of the epoxide was determined by X-ray single crystal structure analysis and it was demonstrated that the epoxide was stereo-isomerically pure.

Preparation method for impurity of oseltamivir synthesis process

The invention provides a preparation method for impurity of an oseltamivir synthesis process. The preparation method comprises the following steps: with shikimic acid as a starting material, successively carrying out an esterification reaction, a Mitsunob

FLOW SYNTHESIS PROCESS FOR THE PRODUCTION OF OSELTAMIVIR

This invention provides for a flow synthesis process for producing Oseltamivir and pharmaceutically acceptable salts thereof from shikimic acid in particular but not exclusively to a flow synthesis process for producing Oseltamivir phosphate from shikimic acid in a nine-step flow synthesis that provides for superior reaction times and product yields compared to known methods.