*,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester

Base Information

• Chemical Name: *,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester
• CAS No.: 144373-38-6
• Molecular Formula: C₂₀H₂₃NO₆S
• Molecular Weight: 405.472

Synonyms:*,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester

Chemical Property of *,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester

Chemical Property:

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Technology Process of *,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester

There total 4 articles about *,R^*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester 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: 49.0%

*,R*)>-2-hydroxy-2-<(methylsulfinyl)methyl>butanedioic acid dibenzyl ester (144373-36-4) → *,R*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester (144373-38-6)

Guidance literature:

With mesitylenesulfonylhydroxylamine; In dichloromethane; at 25 ℃; for 18h;

DOI:10.1021/jm00104a014

Reference yield:

4-(methylthio)-3-oxobutanoic acid methyl ester (64127-51-1) → *,R*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester (144373-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) conc. HCl, 2.) conc. HCl, 3.) 3 N aq. HCl

2: 61 percent / K₂CO₃ / dimethylformamide / 18 h / 60 °C

3: 31 percent / O₃, Sudan III / CH₂Cl₂ / -78 °C

4: 49 percent / O-(mesitylsulfonyl)hydroxylamine / CH₂Cl₂ / 18 h / 25 °C

With hydrogenchloride; oil scarlet; mesitylenesulfonylhydroxylamine; potassium carbonate; ozone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00104a014

Reference yield:

2-hydroxy-2-<(methylthio)methyl>butanedioic acid (144373-33-1) → *,R*)>-2-hydroxy-2-<(S-methylsulfonimidoyl)methyl>butanedioic acid dibenzyl ester (144373-38-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / K₂CO₃ / dimethylformamide / 18 h / 60 °C

2: 31 percent / O₃, Sudan III / CH₂Cl₂ / -78 °C

3: 49 percent / O-(mesitylsulfonyl)hydroxylamine / CH₂Cl₂ / 18 h / 25 °C

With oil scarlet; mesitylenesulfonylhydroxylamine; potassium carbonate; ozone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00104a014

upstream raw materials:

*,R^*)>-2-hydroxy-2-<(methylsulfinyl)methyl>butanedioic acid dibenzyl ester

4-(methylthio)-3-oxobutanoic acid methyl ester

2-hydroxy-2-<(methylthio)methyl>butanedioic acid

2-hydroxy-2-<(methylthio)methyl>butanedioic acid dibenzyl ester

Downstream raw materials:

*-trans)>-4,5-dihydro-4-hydroxy-1-methyl-3-oxo-3H-1λ⁴-isothiazole-4-acetic acid benzyl ester

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