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

Base Information

• Chemical Name: (1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid
• CAS No.: 178435-94-4
• Molecular Formula: C₂₄H₃₀O₃Si
• Molecular Weight: 394.586
• Mol file: 178435-94-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid 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: 91.0%

(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}methanol (178602-56-7) → (1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid (178435-94-4)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 23 ℃; for 1.5h;

DOI:10.1021/ja961093g

Reference yield:

(1S,2R,1'S,2'R)-2,2'-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclopropyl (178602-54-5) → (1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carboxylic acid (178435-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / Bu₄NF / tetrahydrofuran / 2 h / 23 °C

2: 91 percent / RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / 23 °C

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; In tetrahydrofuran; 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) + 2-mercaptopyridine N-oxide (1121-31-9) → (1S,2R,1'S,2'R)-2'-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclopropyl-2-carbothioic acid S-(1-oxy-pyridin-2-yl) ester

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In various solvent(s); at 23 ℃; for 4h;

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

Downstream raw materials:

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

(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

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