(S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester

Base Information

• Chemical Name: (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester
• CAS No.: 1027381-57-2
• Molecular Formula: C₄₃H₅₉NO₄Si
• Molecular Weight: 682.031
• Mol file: 1027381-57-2.mol

Synonyms:(S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester

Chemical Property of (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester

There total 15 articles about (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl 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:

(3S,5R)-5-[(S)-1-Bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-dihydro-furan-2-one → (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester (1027381-57-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / AIBN; NaBH₃CN / tributyltin hydride / benzene; 2-methyl-propan-2-ol / 84 °C

2: DIBAL / CH₂Cl₂ / -78 °C

3: n-BuLi / 0 °C

4: 73 percent / PPh₃; DEAD / diethyl ether / 23 °C

5: trifluoroacetic acid / 0 °C

6: EDCI; HOBt / 23 °C

With n-butyllithium; 2,2'-azobis(isobutyronitrile); diisobutylaluminium hydride; sodium cyanoborohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tri-n-butyl-tin hydride; In diethyl ether; dichloromethane; tert-butyl alcohol; benzene; 3: Wittig reaction / 4: Mitsunobu esterification;

DOI:10.1021/ol049292p

Reference yield:

(2R,4S)-2,4-dimethylpentane-1,5-diol (2121-69-9,54630-82-9,107173-22-8,3817-48-9) → (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester (1027381-57-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / lipase PS-30 / 1,2-dimethoxy-ethane / 23 °C

2: imidazole

3: DIBAL / -78 °C

4: SO₃*pyridine; Et₃N; DMSO / 0 °C

5: n-BuLi / tetrahydrofuran

6: nBu₄NF / tetrahydrofuran

7: PDC / dimethylformamide

8: EDCI; HOBt / 23 °C

With 1H-imidazole; dipyridinium dichromate; n-butyllithium; lipase PS-30; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 5: Wittig reaction;

DOI:10.1021/ol049292p

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-2-[((2R,4S)-2,4-Dimethyl-hex-5-enoyl)-methyl-amino]-3-phenyl-propionic acid (1R,3S)-1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-methyl-pent-4-enyl ester (1027381-57-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / PPh₃; DEAD / diethyl ether / 23 °C

2: trifluoroacetic acid / 0 °C

3: EDCI; HOBt / 23 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In diethyl ether; 2: Mitsunobu esterification;

DOI:10.1021/ol049292p

upstream raw materials:

(2R,4R)-2,4-dimethyl-hex-5-enoic acid

(2R,4S)-2,4-dimethylpentane-1,5-diol

N-tert-butoxycarbonyl-L-phenylalanine

Boc-N-Me-Phe-OH

Downstream raw materials:

(3S,6R,8R,11R,13R)-3-Benzyl-13-(3-hydroxy-propyl)-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridecane-2,5-dione

(Z)-(3S,6R,8S,11S,13R)-3-Benzyl-13-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-4,6,8,11-tetramethyl-1-oxa-4-aza-cyclotridec-9-ene-2,5-dione