[1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester
• CAS No.: 238753-83-8
• Molecular Formula: C₂₄H₄₁NO₃Si
• Molecular Weight: 419.68
• Mol file: 238753-83-8.mol

Synonyms:[1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

Chemical Property of [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester

There total 5 articles about [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic 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: 78.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol (173204-72-3) → [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester (238753-83-8)

Guidance literature:

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

DOI:10.1055/s-1999-2765

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester (238753-83-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaOH / tetrahydrofuran / 2 h / 20 °C

2: 88 percent / tetrahydrofuran / 6 h / -30 °C

3: 78 percent / (i-Pr)2NEt / CH₂Cl₂

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Addition / 3: Etherification;

DOI:10.1055/s-1999-2765

Reference yield:

(R)-1-(oxiran-2-yl)-2-phenylethanone (169057-29-8) → [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester (238753-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / Me₄NBH(OAc)3; CH₃COOH; molecular sieves 4 Angstroem / CH₂Cl₂ / 15 h / 0 °C

2: 75 percent / NaOH / tetrahydrofuran / 2 h / 20 °C

3: 88 percent / tetrahydrofuran / 6 h / -30 °C

4: 78 percent / (i-Pr)2NEt / CH₂Cl₂

With sodium hydroxide; 4 A molecular sieve; acetic acid; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Substitution / 3: Addition / 4: Etherification;

DOI:10.1055/s-1999-2765

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol

di-tert-butyl dicarbonate

(R)-1-(oxiran-2-yl)-2-phenylethanone

Downstream raw materials:

(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid