OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER

Base Information

• Chemical Name: OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER
• CAS No.: 150134-08-0
• Molecular Formula: C₅H₆O₅
• Molecular Weight: 146.1
• Mol file: 150134-08-0.mol

Synonyms:OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER;2,3-Oxiranedicarboxylicacid,monomethylester,(2S-trans)-(9CI);(2S,3S)-3-(METHOXYCARBONYL)OXIRANE-2-CARBOXYLIC ACID;OXIRANE-2,3-DICARBOXYLIC ACID MONOMETHYL ESTER

Chemical Property of OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER

Chemical Property:

• Boiling Point: 434.4 °C at 760 mmHg
• Flash Point: 195.8 °C
• PSA: 76.13000
• Density: 1.676 g/cm³
• LogP: -0.98860

Purity/Quality:

99% ^*data from raw suppliers

OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER

There total 6 articles about OXIRANE-(2S,3S)-DICARBOXYLIC ACID MONOMETHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + cis-2,3-epoxysuccinic anhydride (16191-17-6,34955-54-9) → methyl (2RS,3SR)-2,3-oxiranedicarboxylate (63544-00-3,66647-19-6,96096-72-9,110115-15-6,110115-16-7,112574-71-7,119240-65-2,150134-07-9,150134-08-0)

Guidance literature:

DOI:10.1002/jhet.5570420511

Reference yield: 53.0%

(2R,3S)-dimethyl oxirane-2,3-dicarboxylate (56958-97-5,718617-86-8) → (2S,3R)-Oxirane-2,3-dicarboxylic acid monomethyl ester (63544-00-3,66647-19-6,96096-72-9,110115-15-6,110115-16-7,112574-71-7,119240-65-2,150134-07-9,150134-08-0)

Guidance literature:

for 20h; Ambient temperature; pig-liver esterase, pH 7;

DOI:10.1016/S0040-4039(01)80988-6

Reference yield: 47.0%

(2R,3S)-dimethyl oxirane-2,3-dicarboxylate (56958-97-5,718617-86-8) → methyl (2RS,3SR)-2,3-oxiranedicarboxylate (63544-00-3,66647-19-6,96096-72-9,110115-15-6,110115-16-7,112574-71-7,119240-65-2,150134-07-9,150134-08-0)

Guidance literature:

With enzyme ficin (EC 3.4.22.3); for 20h; Ambient temperature; 0.1M phosphate buffer (pH 7);

DOI:10.1002/jhet.5570250225

upstream raw materials:

(2R,3S)-dimethyl oxirane-2,3-dicarboxylate

tert.-butylhydroperoxide

dimethyl cis-but-2-ene-1,4-dioate

methanol

Downstream raw materials:

(5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-7-oxo-3-(pyridin-4-ylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(2R,5R,6S)-6-((S)-Hydroxy-methoxycarbonyl-methyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

(R)-[(2S,3S)-2-Acetoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl]-(tert-butyl-dimethyl-silanyloxy)-acetic acid methyl ester

(2S,3S)-3-((S)-Hydroxy-methoxycarbonyl-methyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester

Refernces

• 1、 Meth-Cohn, Otto,Moore, Clive,Taljaard, Heinrich C.. "A stereocontrolled approach to electrophilic epoxides". . p. 2663 - 2674. Retrieved 2007/10/02.
• 2、 Haebich, Dieter,Hartwig, Wolfgang. "SYNTHESIS OF A NEW CARBAPENEM WITH A 6-METHYL HYDROXYACETATE SIDE CHAIN". . p. 781 - 784. Retrieved 2007/10/02.