[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-methylsulfonylphenyl)propyl] hexadecanoate

Base Information

• Chemical Name: [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-methylsulfonylphenyl)propyl] hexadecanoate
• CAS No.: 21478-01-3
• Molecular Formula: C28H45 Cl2 N O6 S
• Molecular Weight: 594.64
• Nikkaji Number: J388.272A
• Mol file: 21478-01-3.mol

Synonyms:

Chemical Property of [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-methylsulfonylphenyl)propyl] hexadecanoate

Chemical Property:

• Vapor Pressure: 1.4E-22mmHg at 25°C
• Boiling Point: 733.4°Cat760mmHg
• Flash Point: 397.4°C
• PSA: 118.15000
• Density: 1.168g/cm³
• LogP: 7.90820
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 22
• Exact Mass: 593.2344647
• Heavy Atom Count: 38
• Complexity: 751

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(C(C1=CC=C(C=C1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H]([C@@H](C1=CC=C(C=C1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl

Technology Process of [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-methylsulfonylphenyl)propyl] hexadecanoate

There total 3 articles about [(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-methylsulfonylphenyl)propyl] hexadecanoate 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: 98.0%

vinyl palmitate (693-38-9) + thiamphenicol (15318-45-3,90-91-5) → threo-(1R,2R)-1-<(4-methylsulfonyl)phenyl>-2-(dichloroacetamido)-1,3-propanediol 3-palmitate (21478-01-3)

Guidance literature:

With Candida antarctica Lipase type B; In acetonitrile; at 20 ℃; for 1h; Reagent/catalyst; Solvent; regioselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.5935/0103-5053.20140069

Reference yield: 83.0%

thiamphenicol (15318-45-3,90-91-5) + 2,2,2-trifluoroethyl palmitate (119596-14-4) → threo-(1R,2R)-1-<(4-methylsulfonyl)phenyl>-2-(dichloroacetamido)-1,3-propanediol 3-palmitate (21478-01-3)

Guidance literature:

In acetone; at 45 ℃; for 48h; lipase;

DOI:10.1021/jo00295a025

Reference yield:

(2’R,3’R)-thiamphenicol-1’,3’-diacetate → threo-(1R,2R)-1-<(4-methylsulfonyl)phenyl>-2-(dichloroacetamido)-1,3-propanediol 3-palmitate (21478-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Candida rugosa lipase / acetonitrile; aq. phosphate buffer / 48 h / 20 °C / pH 7 / Enzymatic reaction

2: Candida antarctica Lipase type B / acetonitrile / 1 h / 20 °C / Inert atmosphere; Enzymatic reaction

With Candida antarctica Lipase type B; Candida rugosa lipase; In aq. phosphate buffer; acetonitrile;

DOI:10.5935/0103-5053.20140069

upstream raw materials:

thiamphenicol

2,2,2-trifluoroethyl palmitate

vinyl palmitate