(R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Base Information

• Chemical Name: (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol
• CAS No.: 895153-48-7
• Molecular Formula: C₁₆H₂₄O₃Si
• Molecular Weight: 292.45
• Mol file: 895153-48-7.mol

Synonyms:(R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Chemical Property of (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

There total 2 articles about (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol 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: 83.0%

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane (80910-01-6,108836-41-5,144069-33-0,134733-19-0) + trimethylsilylacetylene (1066-54-2) → (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol (895153-48-7)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1021/acs.orglett.8b01578

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol (895153-48-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.42 h / 0 °C

1.2: 20 h / 23 °C

2.1: acetic acid; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) / tetrahydrofuran; water / 17 h / 0 - 23 °C / Resolution of racemate

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 2 h / -78 °C

With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); n-butyllithium; sodium hydride; acetic acid; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.orglett.8b01578

Reference yield: 95.0%

(R)-1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol (895153-48-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-tert-butyl((1-((4-methoxybenzyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-yl)oxy)dimethylsilane

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1021/acs.orglett.8b01578

upstream raw materials:

(R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane

trimethylsilylacetylene

p-methoxybenzyl chloride

Downstream raw materials:

[(2R,6S)-2-(4-Methoxy-benzyloxymethyl)-6-vinyl-tetrahydro-pyran-(4Z)-ylidenemethyl]-trimethyl-silane

(2R,6S)-4-[1-Iodo-meth-(Z)-ylidene]-2-(4-methoxy-benzyloxymethyl)-6-vinyl-tetrahydro-pyran

2-[(2S,6R)-4-[1-Iodo-meth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol

C₂₀H₃₀O₄Si