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

Base Information

Chemical Name:(S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate
CAS No.:1376330-99-2
Molecular Formula:C₂₉H₄₂O₅SSi
Molecular Weight:530.801
Hs Code.:

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

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

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

There total 7 articles about (S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate 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: 86.0%

: 1376330-97-0
(R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

: 108-98-5
thiophenol

: 1376330-99-2
(S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 14h; Inert atmosphere;
DOI:10.1002/anie.201200871

Reference yield: 0.85%

: 1376330-97-0
(R)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)hept-2-ynoate

: 108-98-5
thiophenol

: 1376330-99-2
(S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate

: C₂₉H₄₂O₅SSi

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 14h; Inert atmosphere;
DOI:10.1021/acs.joc.8b00193

Reference yield:

: 195257-60-4
(2S)-2-[2-(p-methoxybenzyloxy)ethyl]oxirane

: 1376330-99-2
(S,Z)-ethyl 5-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-3-(phenylthio)hept-2-enoate

Guidance literature:: Multi-step reaction with 3 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

3.1: sodium methylate / methanol / 14 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; sodium methylate; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1002/anie.201200871