2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol

Base Information

• Chemical Name: 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol
• CAS No.: 334705-96-3
• Molecular Formula: C₂₃H₃₂O₂Si
• Molecular Weight: 368.591
• Mol file: 334705-96-3.mol

Synonyms:2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol

Chemical Property of 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol

There total 2 articles about 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol 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: 90.0%

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one (75658-86-5) + methyllithium (917-54-4) + tert-butylchlorodiphenylsilane (58479-61-1) → 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol (334705-96-3)

Guidance literature:

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one; methyllithium; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0496042

Reference yield:

allyl diazoacetate (4606-10-4) → 2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol (334705-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / Rh₂((5R)-MEPY)4 / CH₂Cl₂ / 30 h / Heating

2.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2.2: 90 percent / imidazole / diethyl ether; tetrahydrofuran; dimethylformamide / 20 °C

Doyle dirhodium catalyst; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo0496042

Reference yield: 85.0%

2-((1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-2-ol (334705-96-3) → (1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-isopropenylcyclopropane (334705-97-4)

Guidance literature:

With dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1021/jo0496042

upstream raw materials:

(1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one

methyllithium

tert-butylchlorodiphenylsilane

allyl diazoacetate

Downstream raw materials:

(1S,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-isopropenylcyclopropane

(R)-2-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-propionaldehyde

(2R)-2-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)propan-1-ol

(4S)-4-((1R,2R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}cyclopropyl)pentanal