methyl (3R)-3,4-dihydroxybutanoate

Base Information

• Chemical Name: methyl (3R)-3,4-dihydroxybutanoate
• CAS No.: 88246-12-2
• Molecular Formula: C5H10 O4
• Molecular Weight: 134.132
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID50432155
• Nikkaji Number: J931.356G
• Wikidata: Q82246214
• Mol file: 88246-12-2.mol

Synonyms:methyl (3R)-3,4-dihydroxybutanoate;88246-12-2;(R)-3,4-Dihydroxy-butyric acid methyl ester;114819-45-3;Butanoic acid, 3,4-dihydroxy-, methyl ester, (3R)-;Butanoic acid,3,4-dihydroxy-, methyl ester;C5H10O4;SCHEMBL1691447;DTXSID50432155;KCKWOJWPEXHLOQ-SCSAIBSYSA-N;methyl (r)-3,4-dihydroxybutanoate;(R)-methyl 3,4-dihydroxybutanoate;AKOS006288368;AC-18662;(R)-3,4-Dihydroxybutyric acid methyl ester

Chemical Property of methyl (3R)-3,4-dihydroxybutanoate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.458
• Boiling Point: 267.007°C at 760 mmHg
• Flash Point: 114.322°C
• PSA: 66.76000
• Density: 1.22g/cm³
• LogP: -1.09730
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 134.05790880
• Heavy Atom Count: 9
• Complexity: 91

Purity/Quality:

99%, ^*data from raw suppliers

(R)-3,4-DIHYDROXY-BUTYRIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(CO)O
• Isomeric SMILES: COC(=O)C[C@H](CO)O

Technology Process of methyl (3R)-3,4-dihydroxybutanoate

There total 3 articles about methyl (3R)-3,4-dihydroxybutanoate 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:

dimethyl (S)-malate (617-55-0) → D,L-1,2,4-butanetriol (3068-00-6,6810-31-7) + (3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9) + 2-buten-4-olide (497-23-4) + methyl 3,4-dihydroxybutanoate (88246-12-2)

Guidance literature:

With hydrogen; In Dimethyl ether; at 56 - 110 ℃; for 0.5 - 2h; under 120012 Torr; Product distribution / selectivity;

Reference yield:

Methyl 4-chloroacetoacetate (32807-28-6,935731-94-5) → (S)-methyl 2-(propylene oxide-2-yl)acetate (127001-17-6) + methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0) + methyl 3,4-dihydroxybutanoate (88246-12-2)

Guidance literature:

Methyl 4-chloroacetoacetate; With Lactobacillus brevis alcohol dehydrogenase; isopropyl alcohol; at 30 ℃; for 4h; aq. buffer; Enzymatic reaction;

With Mycobacterium sp. GP₁ halohydrin dehalogenase HheB; at 30 ℃; for 20h; optical yield given as %ee; stereoselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.tetasy.2009.02.035

Reference yield:

malic acid dimethyl ester (38115-87-6) → 4-butanolide (96-48-0) + 4-Hydroxy-dihydro-furan-2-on (5469-16-9,7331-52-4,58081-05-3,131432-37-6) + D,L-1,2,4-butanetriol (3068-00-6,6810-31-7) + 3-hydroxyoxolan-2-one (19444-84-9) + methyl 3,4-dihydroxybutanoate (88246-12-2) + methyl 2,4-dihydroxybutanoate (135247-43-7)

Guidance literature:

With hydrogen; In water; at 90 ℃; for 12h; under 60006 Torr; Autoclave;

DOI:10.1007/s10562-021-03877-1

upstream raw materials:

dimethyl (S)-malate

Methyl 4-chloroacetoacetate

malic acid dimethyl ester

Downstream raw materials:

methyl 4-triphenylmethyloxy-3(S)-hydroxybutyrate

4-Hydroxy-dihydro-furan-2-on

(2-Phenyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester

Refernces

• 1、 Schrittwieser, Joerg H.,Lavandera, Ivan,Seisser, Birgit,Mautner, Barbara,Lutje Spelberg, Jeffrey H.,Kroutil, Wolfgang. "Shifting the equilibrium of a biocatalytic cascade synthesis to enantiopure epoxides using anion exchangers". experimental part. p. 483 - 488. Retrieved 2009/07/25.