methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate

Base Information

• Chemical Name: methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate
• CAS No.: 124649-67-8
• Molecular Formula: C10H12 O4
• Molecular Weight: 196.203
• DSSTox Substance ID: DTXSID50431042
• Nikkaji Number: J1.549.598G
• Wikidata: Q82244831
• Mol file: 124649-67-8.mol

Synonyms:124649-67-8;methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate;Methyl (2S,3R)-(-)-2,3-dihydroxy-3-phenylpropionate;(2S,3R)-Methyl 2,3-dihydroxy-3-phenylpropanoate;SCHEMBL6874324;DTXSID50431042;IXDRYSIPXMREGK-BDAKNGLRSA-N;AS-80074;J-005105;Methyl (2S,3R)-(-)-2,3-dihydroxy-3-phenylpropionate, 99%;(alphaS,betaR)-alpha,beta-Dihydroxybenzenepropanoic acid methyl ester;Benzenepropanoic acid, alpha,beta-dihydroxy-, methyl ester, (alphaS,betaR)-

Chemical Property of methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 85-88 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 345.2°Cat760mmHg
• PKA: 12.33±0.20(Predicted)
• Flash Point: 136.6°C
• PSA: 66.76000
• Density: 1.266g/cm³
• LogP: 0.25390
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl(2S,3R)-2,3-Dihydroxy-3-phenylpropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C(C1=CC=CC=C1)O)O
• Isomeric SMILES: COC(=O)[C@H]([C@@H](C1=CC=CC=C1)O)O
• Uses: Methyl (2S,3R)-(?)-2,3-dihydroxy-3-phenylpropionate can be used to synthesize methyl(2R,3R)-2,3-epoxy-3-phenylpropionate, a key intermediate for the preparation of taxol side chain.

Technology Process of methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate

There total 66 articles about methyl (2S,3R)-2,3-dihydroxy-3-phenylpropanoate 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%

Methyl cinnamate (103-26-4,1754-62-7) → methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate (124649-67-8)

Guidance literature:

With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; chiral triazine catalyst; In water; tert-butyl alcohol; at 0 ℃; for 14h;

DOI:10.1016/j.tetlet.2004.09.098

Reference yield: 93.0%

Methyl cinnamate (103-26-4,1754-62-7) → Methyl (2RS,3RS)-2,3-dihydroxy-3-phenylpropionate (65870-46-4,65870-49-7,81691-59-0,122743-18-4,124649-67-8,130796-40-6,143505-39-9)

Guidance literature:

With 4-methylmorpholine N-oxide; polyaniline-supported Os; In water; acetone; acetonitrile; at 20 ℃;

DOI:10.1002/adsc.200606077

Reference yield: 93.0%

iodobenzene (591-50-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate (124649-67-8)

Guidance literature:

iodobenzene; acrylic acid methyl ester; With triethylamine; LDH-PdOsW; at 70 ℃;

With 4-methyl-morpholine; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; dihydrogen peroxide; LDH-PdOsW; In tert-butyl alcohol; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo026687i

upstream raw materials:

Methyl cinnamate

methanol

(2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester

benzaldehyde

Downstream raw materials:

(2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate

(R)-5-((S)-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)(hydroxy)methyl)furan-2(5H)-one

(S)-5-((S)-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)(hydroxy)methyl)furan-2(5H)-one

Refernces

• 1、 Byoung, Se Lee,Mahajan, Suresh,Janda, Kim D.. "Asymmetric dihydroxylation catalyzed by ionic polymer-supported osmium tetroxide". . p. 4491 - 4493. Retrieved 2005.
• 2、 Jonsson, Sandra Y.,Adolfsson, Hans,Baeckvall, Jan-E.. "MTO and OsO4: An efficient catalytic couple for mild H2O2-based asymmetric dihydroxylation of olefins". . p. 2783 - 2788. Retrieved 2003.
• 3、 Motorina, Irina,Crudden, Cathleen M.. "Asymmetric dihydroxylation of olefins using cinchona alkaloids on highly ordered inorganic supports". . p. 2325 - 2328. Retrieved 2001.
• 4、 Blumberg, Shawn,Martin, Stephen F.. "Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions". . p. 7 - 14. Retrieved 2020/10/08.