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

Description

ShikiMic Acid Ethyl Ester is an organic compound that serves as an intermediate in the synthesis of various chemical compounds, particularly in the production of neuraminidase inhibitors.

Uses

Used in Pharmaceutical Industry:
ShikiMic Acid Ethyl Ester is used as a chemical intermediate for the synthesis of (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). This analog is an essential component in the synthesis of neuraminidase inhibitors, which are crucial in the development of antiviral medications.

Upstream product

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

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 
• 77-95-2 D-(-)-quinic acid 
• 191916-39-9 methyl (-)-quinate 
• 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.