(2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate

Base Information

• Chemical Name: (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate
• CAS No.: 66716-31-2
• Molecular Formula: C₁₆H₁₆O₃S
• Molecular Weight: 288.367
• Mol file: 66716-31-2.mol

Synonyms:

Chemical Property of (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate

There total 2 articles about (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate 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:

methyl (phenylsulfanyl)acetate (17277-58-6) + benzaldehyde (100-52-7) → (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate (66716-31-2) + (2RS,3RS)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate (66716-32-3)

Guidance literature:

With zinc(II) chloride; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) -78 deg C, THF, 2) 0 deg C, 10 min;

DOI:10.1021/jo01306a002

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (phenylthio)acetic acid (103-04-8) + benzaldehyde (100-52-7) → (2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate (66716-31-2) + (2RS,3RS)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate (66716-32-3)

Guidance literature:

Multistep reaction; (i) LDA, (ii) /BRN= 471223/, (iii) /BRN= 102415/;

Reference yield:

(2RS,3SR)-methyl 3-hydroxy-2-(phenylthio)benzenepropanoate (66716-31-2) → methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate (58808-66-5)

Guidance literature:

With 2-fluoro-1-ethylpyridinium tetrafluoroborate; triethylamine; lithium iodide; Yield given. Multistep reaction; 1) acetone-d6, 5 min room temperature, 2) 60 deg C, 40 min;

DOI:10.1021/jo01306a002

upstream raw materials:

methyl (phenylsulfanyl)acetate

benzaldehyde

diazomethane

(phenylthio)acetic acid

Downstream raw materials:

methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate

Refernces

• 1、 Hoye, Thomas R.,Kurth, Mark J.. "Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions". . p. 3549 - 3554. Retrieved 2007/10/02.