tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane

Base Information

• Chemical Name: tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane
• CAS No.: 937067-95-3
• Molecular Formula: C₂₁H₂₆O₂Si
• Molecular Weight: 338.522
• Mol file: 937067-95-3.mol

Synonyms:tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane

Chemical Property of tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane

There total 3 articles about tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)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:

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxirane-2-carbaldehyde (131486-44-7) → tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane (937067-95-3)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

(2R,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxirane-2-carbaldehyde; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jo0626461

Reference yield:

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol (92808-78-1) → tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane (937067-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (+)-diethyl L-tartrate; titanium(IV) isopropoxide / CH₂Cl₂ / 0.33 h / -30 - -20 °C

1.2: tert-butyl hydroperoxide / CH₂Cl₂ / 5.5 h / -30 - -20 °C

2.1: Dess-Martin reagent / CH₂Cl₂ / 2.5 h / 20 °C

3.1: KOtBu / tetrahydrofuran / 0.5 h / 0 °C

3.2: 14.0 g / tetrahydrofuran / 2 h / 20 °C

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; potassium tert-butylate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0626461

Reference yield:

((2S,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol (131484-40-7) → tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane (937067-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Dess-Martin reagent / CH₂Cl₂ / 2.5 h / 20 °C

2.1: KOtBu / tetrahydrofuran / 0.5 h / 0 °C

2.2: 14.0 g / tetrahydrofuran / 2 h / 20 °C

With potassium tert-butylate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0626461

upstream raw materials:

Methyltriphenylphosphonium bromide

(2R,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxirane-2-carbaldehyde

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

((2S,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol

Downstream raw materials:

(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-4,8-dimethyl-8-(triethylsilyloxy)-1-nonen-5-one

(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenal

(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-2-methyl-4-pentenenitrile