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

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

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

• 943515-58-0 (3aR,7R,7aS)-ethyl 2,2-diethyl-7-hydroxy-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1132659-94-9 (3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 
• 1149345-83-4 ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 
• 1149345-89-0 ethyl (3R,4R,5R)-4-acetamido-3-(1-ethyl-propoxy)-5-hydroxy-cyclohex-1-ene-1-carboxylate 
• 1350928-99-2 ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-hydroxy-cyclohex-1-ene-1-carboxylate 
• 1350929-01-9 C₁₁H₁₅N₃O₅ 
• 1350929-02-0 ethyl (3S,4R,5R)-3-azido-5-acetoxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 
• 1350929-05-3 ethyl (3R,4R,5R)-4-acetamido-5-acetoxy-3-(1-ethylpropoxy)-cyclohex-1-ene-1-carboxylate 
• 1350928-98-1 C₁₆H₁₆O₇S 
• 1350928-95-8 ethyl (3S,4R,5R)-3-azido-4,5-dihydroxycyclohex-1-ene-1-carboxylate 
• 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 

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

New Method for the Rapid Extraction of Natural Products: Efficient Isolation of Shikimic Acid from Star Anise

A new, practical, rapid, and high-yielding process for the pressurized hot water extraction (PHWE) of multigram quantities of shikimic acid from star anise (Illicium verum) using an unmodified household espresso machine has been developed. This operationa

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.

Method for preparing oseltamivir intermediate

The invention relates to a preparation method of an oseltamivir intermediate (as shown in a formula IV). The method is prepared through a route as described in the specification. The method is simple and safe to operate, short in synthetic route, high in yield, small in environmental pollution, good in economic effect and suitable for industrial production.

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

Crystallization method of intermediate 5 of high-purity oseltamivir phosphate

5 (Pentane 5 -yloxy) -3 - oxo -7 - bicyclo [-] hep 4.1.0-3 -3 - carboxylate ethyl carboxylate is concentrated to precipitate crystals, and then crystals are directly put into a mixed solvent composed of an alkane solvent and an alcohol solvent. Through the crystallization method, the purity of the intermediate 5 can reach above 99.7%, and the requirement for preparing oseltamivir phosphate is completely met.

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.

Synthesis method of daphenanthrene key intermediate

The invention relates to a synthetic method of a Duffy key intermediate. The synthetic method comprises the following steps of by taking shikimic acid as a starting material and performing reactions including esterification reaction, selective oxidation a

The hydrophobic side chain of oseltamivir influences type A subtype selectivity of neuraminidase inhibitors

Neuraminidase, which plays a critical role in the influenza virus life cycle, is a target for new therapeutic agents. The study of structure–activity relationships revealed that the C-5 position amino group of oseltamivir was pointed to 150-cavity of the neuraminidase in group 1. This cavity is important for selectivity of inhibitors against N1 versus N2 NA. A serial of influenza neuraminidase inhibitors with the oseltamivir scaffold containing lipophilic side chains at the C-5 position have been synthesized and evaluated for their influenza neuraminidase inhibitory activity and selectivity. The results indicated that compound 13o (H5N1 IC50?=?0.1?±?0.04?μm, H3N2 IC50?=?0.26?±?0.18?μm) showed better inhibitory activity and selectivity against the group 1 neuraminidase. This study may provide a clue to design of better group 1 neuraminidase inhibitors.

Antioxidant

PROBLEM TO BE SOLVED: To provide an improved antioxidant.SOLUTION: An antioxidant comprises a cyclohexanetriol derivative represented by formula (1) as an active ingredient.