(S)-Methyl 3-hydroxy-2-methylpropanoate

Base Information

• Chemical Name: (S)-Methyl 3-hydroxy-2-methylpropanoate
• CAS No.: 80657-57-4
• Molecular Formula: C5H10O3
• Molecular Weight: 118.133
• Hs Code.: 29181990
• DSSTox Substance ID: DTXSID80436525
• Nikkaji Number: J61.909D
• Wikidata: Q72491328
• Metabolomics Workbench ID: 71694
• Mol file: 80657-57-4.mol

Synonyms:80657-57-4;(S)-Methyl 3-hydroxy-2-methylpropanoate;Methyl (S)-(+)-3-hydroxy-2-methylpropionate;Methyl (2S)-3-hydroxy-2-methylpropanoate;(+)-Methyl L-beta-hydroxyisobutyrate;(S)-(+)-3-Hydroxy-2-methylpropionic Acid Methyl Ester;MFCD00064520;Propanoic acid, 3-hydroxy-2-methyl-, methyl ester, (2S)-;(S)-(+)-Methyl 3-hydroxy-2-methylpropionate;(S)-(+)-3-Hydroxyisobutyric Acid Methyl Ester;methyl(s)-(+)-3-hydroxy-2-methylpropionate;Methyl 3-hydroxy-2-methylpropanoate #;(S)-Roche ester;Roche ester (S);SCHEMBL86348;(S)-3-hydroxy-2-methyl-propionic acid methyl ester;DTXSID80436525;AMY14286;BCP07508;TD8064;(S)-(+)-methyl B-hydroxyisobutyrate;AKOS015850951;CS-W023098;Methyl (S)-(+)-3-Hydroxyisobutyrate;(S)-Methyl3-hydroxy-2-methylpropanoate;methyl (s)-3-hydroxy-2-methylpropanoate;methyl (s)-3-hydroxy-2-methylpropionate;methyl 3-hydroxy-2-(S)-methylpropanoate;Methyl L-(+)-.beta.-hydroxyisobutyrate;AC-31279;AS-18926;(S)-3-Hydroxyisobutyric acid methyl ester;(S)-(+)methyl 3-hydroxy-2-methylpropionate;H0702;Methyl (2S)-3-Hydroxy-2-methyl-propanoate;EN300-85296;(S)-(+)-methyl-3-hydroxy-2-methylpropionate;Methyl (S)-(+)-2-methyl-3-hydroxypropionate;Methyl (S)-(+)-3-hydroxy-2-methyl-propionate;(S)-3-hydroxy-2-methylpropionic acid methyl ester;A839959;Methyl (S)-(+/-)-3-hydroxy-2-methylpropionate;(2S)-3-hydroxy-2-methyl-propionic acid methyl ester;Methyl (S)-(+)-3-hydroxy-2-methylpropionate, 98%;(S)-( +)-3-hydroxy-2-methylpropionic acid methyl ester;Methyl 3-hydroxy-(2S)-methylpropanoate;(2S)-3-Hydroxy-2-methylpropanoic acid methyl ester;(2S)-3-Hydroxy-2-methylpropionic acid methyl ester;(S)-2-Methyl-3-hydroxypropionic acid methyl ester

Chemical Property of (S)-Methyl 3-hydroxy-2-methylpropanoate

Chemical Property:

• Refractive Index: n20/D 1.425
• Boiling Point: 175.048 °C at 760 mmHg
• PKA: 14.40±0.10(Predicted)
• Flash Point: 81.111 °C
• PSA: 46.53000
• Density: 1.051 g/cm³
• LogP: -0.21220
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water. Soluble in methanol.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 79.7

Purity/Quality:

97% ^*data from raw suppliers

Methyl (S)-(+)-3-hydroxy-2-methylpropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CO)C(=O)OC
• Isomeric SMILES: C[C@@H](CO)C(=O)OC
• Uses: Methyl (S)-(+)-3-hydroxy-2-methylpropionate is used as a starting material for the synthesis of dictyostatin, discodermolide and spongidepsin.

Technology Process of (S)-Methyl 3-hydroxy-2-methylpropanoate

There total 10 articles about (S)-Methyl 3-hydroxy-2-methylpropanoate 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: 87.0%

methyl 2-hydroxymethylacrylate (15484-46-5) → 3-hydroxy-(2S)-methylpropionate (80657-57-4,42998-03-8)

Guidance literature:

With diisopropyl{1-[(S)-3,5-dioxa-4-phospha-cyclohepta(2,1-a;3,4-a')dinaphthalen-4-yl]-3-methyl-2-indolyl}phosphine; bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; In dichloromethane; at -40 ℃; for 15h; under 15001.5 Torr; Pressure; Temperature; Concentration; optical yield given as %ee; enantioselective reaction; Reactivity; Inert atmosphere;

DOI:10.1002/adsc.200800209

Reference yield: 75.0%

(S)-3-acetoxy-2-methyl-propionic acid methyl ester (73295-10-0) → 3-hydroxy-(2S)-methylpropionate (80657-57-4,42998-03-8)

Guidance literature:

With potassium carbonate; In methanol; at 5 - 10 ℃; for 1h;

Reference yield:

methyl 2-hydroxymethylacrylate (15484-46-5) → 3-hydroxy-(2S)-methylpropionate (80657-57-4,42998-03-8) + methyl (R)-3-hydroxy-2-methylpropionate (72657-23-9,42998-03-8)

Guidance literature:

With hydrogen; {(-)-1,2-bis(2R,5R)-2,5-dimethylphospholanobenzene(cyclooctadiene)rhodium(l)} triflate; In methanol; at 30 ℃; under 3000.3 Torr; Further Variations:; Catalysts; Product distribution;

DOI:10.1002/adsc.200390009

upstream raw materials:

diazomethane

3-hydroxyisobutyric acid

(S)-(+)-3-hydroxy-2-methyl-propanoic acid

(S)-3-acetoxy-2-methyl-propionic acid methyl ester

Downstream raw materials:

methyl 2(S)-methyl-3-tetrahydropyranyloxypropanoate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

(S)-3-hydroxy-2-methylpropionic acid benzyl ester

methyl (R)-(+)-3-(acetylthio)-2-methylpropanoate

Refernces

• 1、 Nett, Nathalie,Duewel, Sabine,Richter, Alexandra Annelis,Hoebenreich, Sabrina. "Revealing Additional Stereocomplementary Pairs of Old Yellow Enzymes by Rational Transfer of Engineered Residues". . p. 685 - 691. Retrieved 2017/04/11.
• 2、 Cristobal-Lecina, Edgar,Etayo, Pablo,Doran, Sean,Reves, Marc,Martin-Gago, Pablo,Grabulosa, Arnald,Costantino, Andrea R.,Vidal-Ferran, Anton,Riera, Antoni,Verdaguer, Xavier. "MaxPHOS ligand: PH/NH tautomerism and rhodium-catalyzed asymmetric hydrogenations". . p. 795 - 804. Retrieved 2014/04/03.