(S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester
• CAS No.: 93836-48-7
• Molecular Formula: C11H11F3O5S
• Molecular Weight: 312.267
• DSSTox Substance ID: DTXSID001177892
• Nikkaji Number: J1.384.397J
• Mol file: 93836-48-7.mol

Synonyms:(S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester;93836-48-7;SCHEMBL18256487;DTXSID001177892;benzyl (2S)-2-trifluoromethanesulfonyloxypropionate;(S)-2-(Trifluoromethylsulfonyloxy)propionic acid benzyl ester;Phenylmethyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate

Chemical Property of (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 312.02792911
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OCC1=CC=CC=C1)OS(=O)(=O)C(F)(F)F
• Isomeric SMILES: C[C@@H](C(=O)OCC1=CC=CC=C1)OS(=O)(=O)C(F)(F)F

Technology Process of (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester

There total 4 articles about (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl 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: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + benzyl (S)-Lactate (56777-24-3) → (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester (93836-48-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1039/b405344c

Reference yield: 88.0%

benzyl lactate (2051-96-9) + N-ethyl-N,N-diisopropylamine (7087-68-5) → (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester (93836-48-7)

Guidance literature:

With sodium chloride; sodium hydrogencarbonate; trifluoromethanesulfonic acid anhydride; In dichloromethane; water;

Reference yield:

benzyl bromide (100-39-0) → (S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester (93836-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / NaHCO₃ / dimethylformamide / 1 h / 100 °C

2: pyridine / CH₂Cl₂ / 0.5 h / -35 °C

With pyridine; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ardp.19943271111

upstream raw materials:

trifluoromethylsulfonic anhydride

benzyl (S)-Lactate

benzyl bromide

benzyl alcohol

Downstream raw materials:

benzyl (R)-N,N-bis(t-butoxycarbonyl)<15N>alaninate

(R)-N-allyloxyalanine benzyl ether

C₃₃H₃₃NO₉S

C₃₁H₃₁NO₈S