(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester
• CAS No.: 335263-32-6
• Molecular Formula: C₃₅H₅₄Cl₃NO₈
• Molecular Weight: 723.175
• Mol file: 335263-32-6.mol

Synonyms:

Chemical Property of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester

There total 2 articles about (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] 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:

methyl 3-oxohexadecanoate (14427-53-3) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester (335263-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / H₂; (1S)-(+)-10-camphorsulfonic acid / Ru₂Cl₄[(R)-BINAP]2*Et₃N / methanol

2.1: NaOH; MeOH

2.2: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂

2.3: PyBOP; 4-(dimethylamino)pyridine / CH₂Cl₂

With methanol; sodium hydroxide; hydrogen; (+)-10-camphorsulfonic acid; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; In methanol;

DOI:10.7164/antibiotics.54.193

Reference yield:

1,1,1-trichloroethanol (115-20-8) + (R)-β-hydroxyhexadecanoic acid methyl ester (51883-36-4,76898-45-8,127593-22-0,20404-35-7) + 5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester (335263-32-6)

Guidance literature:

(R)-β-hydroxyhexadecanoic acid methyl ester; With methanol; sodium hydroxide;

1,1,1-trichloroethanol; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

5-tert-butyl N-benzyloxycarbonyl-L-glutamate; With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.7164/antibiotics.54.193

Reference yield:

benzotriazol-1-ol (2592-95-2) + (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester (335263-32-6) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[(R)-1-(benzotriazol-1-yloxycarbonylmethyl)-tetradecyl] ester 5-tert-butyl ester (335263-34-8)

Guidance literature:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester; With acetic acid; zinc;

benzotriazol-1-ol; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.7164/antibiotics.54.193

upstream raw materials:

1,1,1-trichloroethanol

(R)-β-hydroxyhexadecanoic acid methyl ester

5-tert-butyl N-benzyloxycarbonyl-L-glutamate

methyl 3-oxohexadecanoate

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[(R)-1-(benzotriazol-1-yloxycarbonylmethyl)-tetradecyl] ester 5-tert-butyl ester

Refernces