(R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester

Base Information

• Chemical Name: (R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester
• CAS No.: 149366-14-3
• Molecular Formula: C₁₄H₂₄Cl₃NO₆S
• Molecular Weight: 440.773
• Mol file: 149366-14-3.mol

Synonyms:

Chemical Property of (R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester

There total 1 articles about (R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl 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: 86.0%

N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester (98303-79-8) + 2-Iodomethyl-propane-1,3-diol → (R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester (149366-14-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.627

Reference yield: 87.0%

(R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester (149366-14-3) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 3-[(R)-2-tert-butoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethylsulfanyl]-2-hexadecanoyloxymethyl-propyl ester (1028277-17-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1248/cpb.41.627

Reference yield:

(R)-3-(3-Hydroxy-2-hydroxymethyl-propylsulfanyl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid tert-butyl ester (149366-14-3) → Hexadecanoic acid 3-[(R)-2-carboxy-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethylsulfanyl]-2-hexadecanoyloxymethyl-propyl ester (149366-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / i-Pr₂NEt, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂

2: 64 percent / trifluoroacetic acid (TFA)

With dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1248/cpb.41.627

upstream raw materials:

N-<<(2,2,2-trichloroethyl)oxy>carbonyl>-L-cysteine tert-butyl ester

Downstream raw materials:

Hexadecanoic acid 3-[(R)-2-tert-butoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethylsulfanyl]-2-hexadecanoyloxymethyl-propyl ester

Hexadecanoic acid 3-[(R)-2-carboxy-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethylsulfanyl]-2-hexadecanoyloxymethyl-propyl ester