METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE

Base Information

• Chemical Name: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE
• CAS No.: 122743-18-4
• Molecular Formula: C10H12 O4
• Molecular Weight: 196.203
• Mol file: 122743-18-4.mol

Synonyms:Benzenepropanoicacid, a,b-dihydroxy-, methyl ester, [R-(R*,S*)]-; Methyl(2R,3S)-2,3-dihydroxy-3-phenylpropionate

Chemical Property of METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 84-88 °C(lit.)
• Boiling Point: 345.2°Cat760mmHg
• Flash Point: 136.6°C
• PSA: 66.76000
• Density: 1.266g/cm³
• LogP: 0.25390

Purity/Quality:

98% ^*data from raw suppliers

Methyl (2R,3S)-(+)-2,3-dihydroxy-3-phenylpropionate 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl (2R,3S)-(+)-2,3-dihydroxy-3-phenylpropionate can be used as an intermediate in the synthesis of:Biologically important 5-phenyl substituted Δ2-thiazolines.An antidepressant, (+)-(S)-dapoxetine.(R)-Cyclohexyl lactic acid, a building block required for the preparation of an E-selectin inhibitor.

Technology Process of METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE

There total 37 articles about METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE 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 (2R,3S)-2,3-dihydroxy-3-phenylpropanoate (122743-18-4)

Guidance literature:

With 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 10h;

DOI:10.1021/jo048937w

Reference yield: 94.0%

(6R*,7R*,15S*)-15-<(S*)-(Hydroxy)phenylmethyl>-1,8,13,16-tetraoxadispiro<5.0.5.4>hexadecan-14-one → 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) + (6R,7R)-1,8,13,16-Tetraoxa-dispiro[5.0.5.4]hexadecane

Guidance literature:

With camphor-10-sulfonic acid; In methanol; ethylene glycol; for 4h; Heating;

DOI:10.1039/a900951e

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

upstream raw materials:

Methyl cinnamate

methanol

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

benzaldehyde

Downstream raw materials:

(2R,3S)-2,3-Dihydroxy-N-<(2'RS)-2'-hydroxy-2'-phenylethyl>-N-methylpropanamide

(2R,3S)-2,3-dihydroxy-3-phenylpropionamide

(4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester

(2R,3S)-3-phenylisoserine hydrochloride

Refernces

• 1、 Serbanovic, Ana,Branco, Luis C.,Nunes Da Ponte, Manuel,Afonso, Carlos A.M.. "Osmium catalyzed asymmetric dihydroxylation of methyl trans-cinnamate in ionic liquids, followed by supercritical CO2 product recovery". . p. 3600 - 3608. Retrieved 2005.
• 2、 Song, Choong Eui,Oh, Chun Rim,Roh, Eun Joo,Choi, Jung Hoon. "Asymmetric dihydroxylation of trans-cinnamates under high-pressure conditions: Substantial increase of turnover number". . p. 1533 - 1535. Retrieved 2001.
• 3、 Song, Choong Eui,Yang, Jung Woon,Ha, Hyun Joon,Lee, Sang-Gi. "Efficient and practical polymeric catalysts for heterogeneous asymmetric dihydroxylation of olefins". . p. 645 - 648. Retrieved 1996.
• 4、 Hüttel, Stephan,Testolin, Giambattista,Herrmann, Jennifer,Planke, Therese,Gille, Franziska,Moreno, Maria,Stadler, Marc,Br?nstrup, Mark,Kirschning, Andreas,Müller, Rolf. "Discovery and Total Synthesis of Natural Cystobactamid Derivatives with Superior Activity against Gram-Negative Pathogens". . p. 12760 - 12764. Retrieved 2017.
• 5、 Kaur, Amanpreet,Singh, Vasundhara. "Ionophilic imidazolium-tagged cinchona ligand on LDH-immobilized osmium: Recyclable and recoverable catalytic system for asymmetric dihydroxylation reaction of olefins". . p. 1191 - 1194. Retrieved 2015.
• 6、 Planke, Therese,Moreno, María,Hüttel, Stephan,Fohrer, J?rg,Gille, Franziska,Norris, Matthew D.,Siebke, Maik,Wang, Liangliang,Müller, Rolf,Kirschning, Andreas. "Cystobactamids 920-1 and 920-2: Assignment of the Constitution and Relative Configuration by Total Synthesis". supporting information. p. 1359 - 1363. Retrieved 2019/03/08.