(R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

Base Information

• Chemical Name: (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate
• CAS No.: 1376330-97-0
• Molecular Formula: C₂₃H₃₆O₅Si
• Molecular Weight: 420.621
• Mol file: 1376330-97-0.mol

Synonyms:(R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

Chemical Property of (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

There total 5 articles about (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate 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: 98.0%

(R)-ethyl 5-hydroxy-7-((4-methoxybenzyl)oxy)hept-2-ynoate (1376331-16-6) + t-butyldimethylsiyl triflate (69739-34-0) → (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate (1376330-97-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.8b00193

Reference yield:

(2S)-2-[2-(p-methoxybenzyloxy)ethyl]oxirane (195257-60-4) → (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate (1376330-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

1.2: -75 - 70 °C / Inert atmosphere

1.3: 0.75 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/anie.201200871

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate (1376330-97-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.17 h / -16 - -5 °C / Inert atmosphere

1.2: 3.25 h / -16 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: -75 - 70 °C / Inert atmosphere

2.3: 0.75 h / -78 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; dichloromethane; mineral oil;

DOI:10.1002/anie.201200871

upstream raw materials:

(R)-ethyl 5-hydroxy-7-((4-methoxybenzyl)oxy)hept-2-ynoate

t-butyldimethylsiyl triflate

p-Methoxybenzyl bromide

4-Methoxybenzyl alcohol

Downstream raw materials:

(R,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-methylhept-2-enoate

(R,E)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-methylhept-2-enoate

(S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate

(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl propionate