Benzenesulfonic acid, 4-bromo-, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]cyclobutyl ester, cis-

Base Information

• Chemical Name: Benzenesulfonic acid, 4-bromo-, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]cyclobutyl ester, cis-
• CAS No.: 141352-69-4
• Molecular Formula: C27H31BrO4SSi
• Molecular Weight: 559.596
• Mol file: 141352-69-4.mol

Synonyms:

Chemical Property of Benzenesulfonic acid, 4-bromo-, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]cyclobutyl ester, cis-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenesulfonic acid, 4-bromo-, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]cyclobutyl ester, cis-

There total 8 articles about Benzenesulfonic acid, 4-bromo-, 3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]cyclobutyl ester, cis- 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: 76.2%

3α-<((tert-butyl)diphenylsilyloxy)methyl>cyclobutane-1α-ol (141352-67-2) + 4-bromobenzenesulfonyl chloride (98-58-8) → 3α-<((tert-butyl)diphenylsilyloxy)methyl>cyclobut-1α-yl 4-bromobenzenesulfonate (141352-69-4)

Guidance literature:

With triethylamine; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1002/hlca.19920750216

Reference yield:

diethyl 3-(benzyloxy)cyclobutane-1,1-dicarboxylate (54166-15-3) → 3α-<((tert-butyl)diphenylsilyloxy)methyl>cyclobut-1α-yl 4-bromobenzenesulfonate (141352-69-4)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. 4M KOH / H₂O; ethanol / 5 h / Heating

2: 88.6 percent / 215 °C / 0.4 Torr

3: 99.5 percent / oxalyl chloride / CCl₄ / 1) 0 deg C, 1 h, 2) r.t., 12 h

4: CCl₄ / 5 h / Ambient temperature

5: 91.9 percent / LiAlH₄ / 1,2-dimethoxy-ethane / 60 h / 85 °C

6: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

7: 99.2 percent / H₂ / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature

8: 76.2 percent / Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19920750216

Reference yield:

3-(benzyloxy)cyclobutane-1,1-dicarboxylic acid (84182-46-7) → 3α-<((tert-butyl)diphenylsilyloxy)methyl>cyclobut-1α-yl 4-bromobenzenesulfonate (141352-69-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 88.6 percent / 215 °C / 0.4 Torr

2: 99.5 percent / oxalyl chloride / CCl₄ / 1) 0 deg C, 1 h, 2) r.t., 12 h

3: CCl₄ / 5 h / Ambient temperature

4: 91.9 percent / LiAlH₄ / 1,2-dimethoxy-ethane / 60 h / 85 °C

5: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

6: 99.2 percent / H₂ / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature

7: 76.2 percent / Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19920750216

upstream raw materials:

3α-<((tert-butyl)diphenylsilyloxy)methyl>cyclobutane-1α-ol

4-bromobenzenesulfonyl chloride

3-(benzyloxy)cyclobutane-1,1-dicarboxylic acid

3-(benzyloxy)cyclobutane-1-carboxylic acid

Downstream raw materials:

9-<3α-(((tert-butyl)diphenylsilyloxy)methyl)cyclobut-1β-yl>-9H-purin-6-amine

3β-(6-amino-9H-purin-9-yl)cyclobutane-1α-methanol