[2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane
• CAS No.: 144125-92-8
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 144125-92-8.mol

Synonyms:[2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane

Chemical Property of [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane

There total 2 articles about [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-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: 90.0%

benzyl bromide (100-39-0) + (2S,3R)-4-t-butyldimethylsilyloxy-2,3-epoxy-pentan-1-ol (111466-32-1) → [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane (144125-92-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89856-2

Reference yield:

(Z)-5-<(1,1-dimethylethyl)dimethylsilyloxy>pent-2-en-1-ol (86462-75-1) → [2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane (144125-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl (+)-L-tartrate / Sharpless epoxidation

2: 90 percent / NaH, Bu₄NI / tetrahydrofuran

With diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89856-2

Reference yield:

[2-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-ethoxy]-tert-butyl-dimethyl-silane (144125-92-8) → N-[(1S,2R)-3-Benzyloxy-1-(2-hydroxy-ethyl)-2-methyl-propyl]-4-methyl-benzenesulfonamide (144076-07-3)

Guidance literature:

Multi-step reaction with 3 steps

2: 97 percent / pyridine / 0.33 h / 0 °C

3: 65 percent / toluene; hexane / 24 h / Heating

With pyridine; In hexane; toluene;

DOI:10.1016/S0040-4020(01)89856-2

upstream raw materials:

benzyl bromide

(2S,3R)-4-t-butyldimethylsilyloxy-2,3-epoxy-pentan-1-ol

(Z)-5-<(1,1-dimethylethyl)dimethylsilyloxy>pent-2-en-1-ol

Downstream raw materials:

2-((2S,3S)-3-Benzyloxymethyl-aziridin-2-yl)-ethanol

N-[(1S,2R)-3-Benzyloxy-1-(2-hydroxy-ethyl)-2-methyl-propyl]-4-methyl-benzenesulfonamide

2-[(2S,3S)-3-Benzyloxymethyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-ethanol

(S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one