tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate

Base Information

• Chemical Name: tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate
• CAS No.: 1305173-72-1
• Molecular Formula: C₃₂H₄₃NO₄Si
• Molecular Weight: 533.783
• Mol file: 1305173-72-1.mol

Synonyms:tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate

Chemical Property of tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate

There total 2 articles about tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate 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:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3-oxopropyl)carbamate (1305173-69-6) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate (1305173-72-1)

Guidance literature:

In chloroform; at 60 ℃; for 9h;

DOI:10.1016/j.tetlet.2010.11.162

Reference yield:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate (1305173-66-3) → tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate (1305173-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst_.(R). 15 / water; acetone / 3 h

2: chloroform / 9 h / 60 °C

With Amberlyst 15; In chloroform; water; acetone; 2: Wittig reaction;

DOI:10.1016/j.tetlet.2010.11.162

Reference yield:

tert-butyl (E)-4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl((E)-5-oxopent-3-enyl)carbamate (1305173-72-1) → (3RS,4RS)-tert-butyl 4-((SR)-1-(benzyl(benzyloxycarbonyl)amino)-5-tert-butyldimethylsilyloxy-4-oxopentan-2-yl)-3-((tert-butyldiphenylsilyloxy)methyl)piperidine-1-carboxylate

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

2.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 24 h / Reflux

3.1: sodium triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

4.1: 1H-imidazole / dichloromethane / 20 °C

5.1: triethylamine / dichloromethane / 20 °C

6.1: ozone / dichloromethane / 0.08 h / -78 °C

6.2: -78 - 20 °C

7.1: sodium tetrahydroborate / ethanol; dichloromethane / -78 °C

8.1: 1H-imidazole / dichloromethane / 20 °C

With 1H-imidazole; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methyl-phenol; sodium triacetoxyborohydride; tetrabutyl ammonium fluoride; ozone; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 2.1: Diels-Alder reaction;

DOI:10.1016/j.tetlet.2010.11.162

upstream raw materials:

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3,3-diethoxypropyl)carbamate

(E)-tert-butyl 4-[(tert-butyldiphenylsilyloxy)methyl]penta-2,4-dienyl(3-oxopropyl)carbamate

(triphenylphosphoranylidene)acetaldehyde