methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate

Base Information

• Chemical Name: methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate
• CAS No.: 189291-10-9
• Molecular Formula: C₁₄H₂₁NO₅S
• Molecular Weight: 315.39
• Mol file: 189291-10-9.mol

Synonyms:methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate

Chemical Property of methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate

There total 1 articles about methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate 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:

methanol (67-56-1) + 2-mesitylenesulphonyl chloride (773-64-8) + D-allo-threonine (24830-94-2,134357-96-3,7013-32-3,82822-12-6) → methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate (189291-10-9)

Guidance literature:

With thionyl chloride; triethylamine; Yield given. Multistep reaction; 1) -78 deg C, --> rt, 18 h; 2) DMF, CHCl3, 0 deg C, 2 h;

DOI:10.1021/jo962094u

Reference yield: 88.0%

methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate (189291-10-9) → methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate (189291-11-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 6h;

DOI:10.1021/jo962094u

Reference yield:

methyl (2R,3R)-N-[(2,4,6-trimethylphenyl)sulfonyl]allothreoninate (189291-10-9) → (Z)-3-[(2S,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid methyl ester (189291-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 6 h / 0 °C

2: diisobutylaluminum hydride / toluene / 2 h / -78 °C

3: 30 percent / toluene / 1 h / -78 - 20 °C

With diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1021/jo962094u

upstream raw materials:

methanol

2-mesitylenesulphonyl chloride

D-allo-threonine

Downstream raw materials:

methyl (2R,3S)-3-methyl-N-[(2,4,6-trimethylphenyl)sulfonyl]-2-aziridinecarboxylate

(Z)-3-[(2S,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid methyl ester

(E)-3-[(2S,3S)-3-Methyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid methyl ester