4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride

Base Information

• Chemical Name: 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride
• CAS No.: 817602-44-1
• Molecular Formula: C₁₃H₁₉ClO₃Si
• Molecular Weight: 286.831
• Mol file: 817602-44-1.mol

Synonyms:4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride

Chemical Property of 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride

There total 1 articles about 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride 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:

phosgene (75-44-5) + 4-(tert-butyldimethylsilyloxy)phenol (108534-47-0) → 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride (817602-44-1)

Guidance literature:

With triethylamine; In diethyl ether; toluene; at 0 ℃; for 2h;

DOI:10.1021/ja0459330

Reference yield:

4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride (817602-44-1) + 5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid tert-butoxycarbonylmethyl ester (817602-43-0) → 4-(4-tert-butoxycarbonylmethoxycarbonyl-butyl)-2-oxo-hexahydro-thieno[3,4-d]imidazole-1-carboxylic acid 4-(tert-butyl-dimethyl-silanyloxy)-phenyl ester (817602-45-2)

Guidance literature:

5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid tert-butoxycarbonylmethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -10 ℃; for 0.0833333h;

4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride; In tetrahydrofuran; for 1h;

DOI:10.1021/ja0459330

Reference yield:

4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride (817602-44-1) → (3aS,4S,6aR)-4-[4-(2-{2-[2-((S)-5-[1,2]Dithiolan-3-yl-pentanoyloxy)-ethoxy]-ethoxy}-ethoxycarbonylmethoxycarbonyl)-butyl]-2-oxo-hexahydro-thieno[3,4-d]imidazole-1-carboxylic acid 4-(tert-butyl-dimethyl-silanyloxy)-phenyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran / 0.08 h / -10 °C

1.2: tetrahydrofuran / 1 h

2.1: 100 percent / trifluoroacetic acid / CHCl₃ / 15 h / 20 °C

3.1: 64 percent / DCC; DMAP / CHCl₃ / 24 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; chloroform;

DOI:10.1021/ja0459330

upstream raw materials:

phosgene

4-(tert-butyldimethylsilyloxy)phenol

Downstream raw materials:

4-(4-tert-butoxycarbonylmethoxycarbonyl-butyl)-2-oxo-hexahydro-thieno[3,4-d]imidazole-1-carboxylic acid 4-(tert-butyl-dimethyl-silanyloxy)-phenyl ester

4-(4-carboxymethoxycarbonyl-butyl)-2-oxo-hexahydro-thieno[3,4-d]imidazole-1-carboxylic acid 4-(tert-butyl-dimethyl-silanyloxy)-phenyl ester

Refernces