Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester

Base Information

• Chemical Name: Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester
• CAS No.: 181368-99-0
• Molecular Formula: C₄₃H₅₃NO₅SSi
• Molecular Weight: 724.049
• Mol file: 181368-99-0.mol

Synonyms:Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester

Chemical Property of Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester

There total 15 articles about Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-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: 87.0%

Methanesulfonic acid (2S,3S)-3-[2-[acetyl-(toluene-4-sulfonyl)-amino]-5-(tert-butyl-diphenyl-silanyloxymethyl)-benzyl]-2-(3,4-dimethyl-pent-3-enyl)-oxiranylmethyl ester (181368-98-9) → Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester (181368-99-0)

Guidance literature:

With sodium iodide; zinc; In N,N-dimethyl-formamide; at 100 ℃; for 0.25h;

DOI:10.1016/0040-4020(96)00608-4

Reference yield:

ethyl 4-amino-3-(2-propenyl)benzoate (59816-84-1) → Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester (181368-99-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / pyridine / CH₂Cl₂ / 17 h / Ambient temperature

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

3: 82 percent / imidazole / dimethylformamide / 85 h / 60 °C

4: 1.) aq. OsO₄, 2.) NaIO₄ / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

5: 87 percent / CH₂Cl₂ / 52 h / Ambient temperature

6: 92 percent / DIBALH / toluene / 0.5 h / -15 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: aq. citric acid*H₂O / diethyl ether; methanol / 0.83 h / Ambient temperature

10: L-(+)-diethyl tartrate, Ti(O-Pr)4, tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

11: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12: 87 percent / Zn, NaI / dimethylformamide / 0.25 h / 100 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; triethylamine; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4020(96)00608-4

Reference yield:

methyl 5,6-dimethyl-2-triphenylphosphoranylidene-5-heptenoate (119139-47-8) → Acetic acid (S)-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonylamino)-benzyl]-5,6-dimethyl-2-methylene-hept-5-enyl ester (181368-99-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / CH₂Cl₂ / 52 h / Ambient temperature

2: 92 percent / DIBALH / toluene / 0.5 h / -15 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: aq. citric acid*H₂O / diethyl ether; methanol / 0.83 h / Ambient temperature

6: L-(+)-diethyl tartrate, Ti(O-Pr)4, tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

7: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 87 percent / Zn, NaI / dimethylformamide / 0.25 h / 100 °C

With tert.-butylhydroperoxide; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; triethylamine; citric acid; sodium iodide; zinc; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0040-4020(96)00608-4

upstream raw materials:

Methanesulfonic acid (2S,3S)-3-[2-[acetyl-(toluene-4-sulfonyl)-amino]-5-(tert-butyl-diphenyl-silanyloxymethyl)-benzyl]-2-(3,4-dimethyl-pent-3-enyl)-oxiranylmethyl ester

ethyl 4-amino-3-(2-propenyl)benzoate

methyl 5,6-dimethyl-2-triphenylphosphoranylidene-5-heptenoate

5-(tert-butyldiphenylsilyl)oxymethyl-1-(p-toluenesulfonyl)-2-indolinole

Downstream raw materials:

(2S)-1-<5-(tert-butyldiphenylsilyl)oxymethyl-2-(p-toluenesulfonyl)aminophenyl>-6,7-dimethyl-3-methylene-6-octen-2-ol

(2S,3R)-1-<5-(tert-butyldiphenylsilyl)oxymethyl-2-(p-toluenesulfonyl)aminophenyl>-3-(3,4-dimethyl-3-pentenyl)-3,4-epoxy-2-butanol

(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-hydroxymethyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde