tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane
• CAS No.: 216494-27-8
• Molecular Formula: C₂₂H₂₉ClO₂Si
• Molecular Weight: 389.01
• Mol file: 216494-27-8.mol

Synonyms:tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

There total 6 articles about tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-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:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane (216494-27-8)

Guidance literature:

With N-chloro-succinimide; triphenylphosphine; In dichloromethane; Heating;

DOI:10.1021/ja982572d

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane (216494-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 10 h / -20 °C / Molecular sieve

2: tetrachloromethane; sodium hydrogencarbonate; triphenylphosphine / Reflux

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; diethyl (2S,3S)-tartrate; sodium hydrogencarbonate; triphenylphosphine; In dichloromethane;

DOI:10.1016/j.tetlet.2018.08.041

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane (216494-27-8)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 5 h / Inert atmosphere; Reflux

2: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / 0 °C / Inert atmosphere

3: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 10 h / -20 °C / Molecular sieve

4: tetrachloromethane; sodium hydrogencarbonate; triphenylphosphine / Reflux

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; In dichloromethane; toluene; benzene;

DOI:10.1016/j.tetlet.2018.08.041

upstream raw materials:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate

Downstream raw materials:

(3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol

C₂₈H₄₂O₃Si₂

C₂₈H₄₃IO₃Si₂

Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester