1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane

Base Information

• Chemical Name: 1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane
• CAS No.: 139242-80-1
• Molecular Formula: C₂₁H₂₈O₃SSi
• Molecular Weight: 388.603
• Mol file: 139242-80-1.mol

Synonyms:1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane

Chemical Property of 1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane

There total 9 articles about 1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane 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: 65.0%

iodo(trimethylsilyl)methane (4206-67-1) + (1S,2R)-2-benzyloxymethylcyclopropyl phenyl sulfone (1233934-54-7) → 1-phenylsulfonyl-1-trimethylsilylmethyl-2-benzyloxymethylcyclopropane (139242-80-1)

Guidance literature:

(1S,2R)-2-benzyloxymethylcyclopropyl phenyl sulfone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.533333h;

iodo(trimethylsilyl)methane; In tetrahydrofuran; at -78 - 20 ℃; for 3.03333h;

DOI:10.1021/jo100844g

Reference yield:

(2S)-1-(Phenylmethoxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentyl methanesulfonate (139242-78-7,139344-62-0) → (2R)-1-(Phenylsulfonyl)-1-<(trimethylsilyl)methyl>-2-<(phenylmethoxy)methyl>cyclopropane (139242-80-1,139242-81-2)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; a.) -78 deg C to r.t., b.) r.t., 3 h;

DOI:10.1021/jo00034a050

Reference yield:

phenyl 2-(trimethylsilyl)ethyl sulfide (17988-59-9) → (2R)-1-(Phenylsulfonyl)-1-<(trimethylsilyl)methyl>-2-<(phenylmethoxy)methyl>cyclopropane (139242-80-1,139242-81-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 30percent hydrogen peroxide, glacial acetic acid / 2 h / 100 °C

2: 1. n-butyllithium / 1. Et₂O, -78 deg C, 20 min; 2. Et₂O, -78 deg C to r.t.

3: Et₃N / CH₂Cl₂ / Ambient temperature

4: n-butyllithium, diisopropylamine / tetrahydrofuran; hexane / a.) -78 deg C to r.t., b.) r.t., 3 h

With n-butyllithium; dihydrogen peroxide; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo00034a050

upstream raw materials:

(2S)-1-(Phenylmethoxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentyl methanesulfonate

phenyl 2-(trimethylsilyl)ethyl sulfide

1-benzenesulfonyl-2-trimethylsilylethane

benzyl bromide

Downstream raw materials:

1-({[(1S)-2-methylenecyclopropyl]methoxy}methyl)benzene

(1R)-<2-(Phenylsulfonyl)-2-<(trimethylsilyl)methyl>cyclopropyl>methyl methanesulfonate

(1S)-<2-(Phenylsulfonyl)-2-<(trimethylsilyl)methyl>cyclopropyl>acetonitrile

(1R,2RS)-<2-phenylsulfonyl-2-<(trimethylsilyl)methyl>cyclopropyl>methanol