dimethyl (2S,3R)-3-methyl-2-O-tosylmalate

Base Information

• Chemical Name: dimethyl (2S,3R)-3-methyl-2-O-tosylmalate
• CAS No.: 369365-14-0
• Molecular Formula: C₁₄H₁₈O₇S
• Molecular Weight: 330.359
• Mol file: 369365-14-0.mol

Synonyms:dimethyl (2S,3R)-3-methyl-2-O-tosylmalate

Chemical Property of dimethyl (2S,3R)-3-methyl-2-O-tosylmalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (2S,3R)-3-methyl-2-O-tosylmalate

There total 3 articles about dimethyl (2S,3R)-3-methyl-2-O-tosylmalate 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: 90.0%

(2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester (50460-80-5,64864-56-8,73889-80-2,77398-86-8,78512-74-0,89104-81-4,150024-71-8,73890-17-2) + p-toluenesulfonyl chloride (98-59-9) → dimethyl (2S,3R)-3-methyl-2-O-tosylmalate (369365-14-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2006.11.171

Reference yield:

(2S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester (50460-80-5,64864-56-8,73889-80-2,73890-17-2,77398-86-8,78512-74-0,89104-81-4,150024-71-8) + p-toluenesulfonyl chloride (98-59-9) → (2S,3S)-2-Methyl-3-(toluene-4-sulfonyloxy)-succinic acid dimethyl ester + dimethyl (2S,3R)-3-methyl-2-O-tosylmalate (369365-14-0)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 30h;

DOI:10.1016/j.tetlet.2005.12.012

Reference yield:

dimethyl (S)-malate (617-55-0) → dimethyl (2S,3R)-3-methyl-2-O-tosylmalate (369365-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / LHMDS / tetrahydrofuran / -78 °C

2: 90 percent / Et₃N; DMAP / CH₂Cl₂

With dmap; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2006.11.171

upstream raw materials:

(2S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester

p-toluenesulfonyl chloride

(2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester

dimethyl (S)-malate

Downstream raw materials:

dimethyl (2R,3R)-2-methyl-3-phenylsultanylsuccinate

(R)-2-methylbutane-1,4-diyl bis(4-methylbenzenesulfonate)

(R)-2-methylbutane-1,4-diol dibenzoate

(S)-dimethyl 2-methylsuccinate

Refernces

• 1、 Chandrasekhar,Rambabu,Prakash, S. Jaya. "Total synthesis of 6-epiprelactone-V via a syn-selective oxygen tethered intramolecular Michael reaction". . p. 1213 - 1215. Retrieved 2007/10/03.