((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane
• CAS No.: 178435-95-5
• Molecular Formula: C₂₃H₂₉BrOSi
• Molecular Weight: 429.472
• Mol file: 178435-95-5.mol

Synonyms:((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property of ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane

There total 4 articles about ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane 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:

(1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carbothioic acid S-(1-oxy-pyridin-2-yl) ester → ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane (178435-95-5) + ((1R,2R,1'S,2'S)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane

Guidance literature:

With Bromotrichloromethane; at 0 ℃; for 1.5h; Yield given; Irradiation;

DOI:10.1021/ja961093g

Reference yield:

(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}methanol (178602-56-7) → ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane (178435-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / 23 °C

2: DCC, DMAP / various solvent(s) / 4 h / 23 °C

3: BrCCl₃ / 1.5 h / 0 °C / Irradiation

With dmap; ruthenium trichloride; sodium periodate; Bromotrichloromethane; dicyclohexyl-carbodiimide; In tetrachloromethane; water; acetonitrile;

DOI:10.1021/ja961093g

Reference yield:

(1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid (178435-94-4) → ((1R,2R,1'S,2'R)-2'-Bromo-bicyclopropyl-2-ylmethoxy)-tert-butyl-diphenyl-silane (178435-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, DMAP / various solvent(s) / 4 h / 23 °C

2: BrCCl₃ / 1.5 h / 0 °C / Irradiation

With dmap; Bromotrichloromethane; dicyclohexyl-carbodiimide; In various solvent(s);

DOI:10.1021/ja961093g

upstream raw materials:

(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}methanol

(1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid

(1S,2R,1'S,2'R)-2,2'-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclopropyl

Downstream raw materials:

(1S,2R,1'R,2'R,1''R,2''R,1'''S,2'''R)-2,2'''-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-[1,1';2',1'';2'',1''']quatercyclopropane

[(1S,2R,1'R,2'R,1''R,2''R,1'''S,2'''R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,1';2',1'';2'',1''']quatercyclopropan-2'''-yl]-methanol