(2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane

Base Information

• Chemical Name: (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane
• CAS No.: 1412945-22-2
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 1412945-22-2.mol

Synonyms:

Chemical Property of (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane

There total 5 articles about (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane 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:

tert-butyldimethylsilyl chloride (18162-48-6) + ((2R,3R)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)methanol (242808-65-7) → (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane (1412945-22-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1055/s-0032-1316734

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane (1412945-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: ethyl bromide; magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 12 h / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

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

5.1: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; ethyl bromide; diethyl (2S,3S)-tartrate; sodium hydride; magnesium; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 4.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1055/s-0032-1316734

Reference yield:

(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol (158817-21-1) → (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(4-Methoxybenzyloxy)ethyl]oxirane (1412945-22-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; In dichloromethane; toluene; 1: |Sharpless Asymmetric Epoxidation;

DOI:10.1055/s-0032-1316734

upstream raw materials:

p-Methoxybenzyl bromide

tert-butyldimethylsilyl chloride

((2R,3R)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)methanol

1-but-3-ynyloxymethyl-4-methoxy-benzene

Downstream raw materials:

(2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-[2-(tosyloxy)ethyl]oxirane