(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

Base Information

Chemical Name:(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole
CAS No.:1612233-48-3
Molecular Formula:C₂₃H₃₃NO₂SSi
Molecular Weight:415.672
Hs Code.:

Synonyms:(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

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Chemical Property of (S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

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Technology Process of (S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

There total 9 articles about (S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole 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: 59.0%

: 1612233-46-1
(S)-tert-butyldimethyl((4-methyl-7-(tributylstannyl)hept-5-yn-1-yl)oxy)silane

: 1612233-47-2
5-iodo-2-(phenylsulfanyl)oxazole

: 1612233-48-3
(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

Guidance literature:: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In N,N-dimethyl-formamide; at 20 ℃; for 18h; regioselective reaction; Inert atmosphere;
DOI:10.1021/ja5043462

Reference yield:

: 618096-59-6
(S)-5-((tert-butyldimethylsilyl)oxy)-2-methylpentan-1-ol

: 1612233-48-3
(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

Guidance literature:: Multi-step reaction with 6 steps

1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 6 h / 20 °C / Inert atmosphere

2.1: triphenylphosphine / dichloromethane / 3 h / 0 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: titanium(IV) isopropylate; isopropylmagnesium chloride / diethyl ether / 2 h / -50 - 30 °C / Inert atmosphere

5.2: 3 h / -78 - 20 °C / Inert atmosphere

6.1: triphenyl-arsane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With pyridine; titanium(IV) isopropylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; triphenyl-arsane; isopropylmagnesium chloride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6.1: |Stille Cross Coupling;
DOI:10.1021/ja5043462

Reference yield:

: 78878-05-4
1-iodo-3-(tert-butyldimethylsilyloxy)propane

: 1612233-48-3
(S)-5-(7-((tert-butyldimethylsilyl)oxy)-4-methylhepta-1,2-dien-3-yl)-2-(phenylthio)oxazole

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium chloride; diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.67 h / -78 - 20 °C / Inert atmosphere

1.2: 18 h / 0 °C / Inert atmosphere

2.1: diisopropylamine; n-butyllithium; ammonia borane / tetrahydrofuran; hexane / 2 h / -78 - 20 °C / Inert atmosphere

3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 6 h / 20 °C / Inert atmosphere

4.1: triphenylphosphine / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

5.2: 12 h / -78 - 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.1: titanium(IV) isopropylate; isopropylmagnesium chloride / diethyl ether / 2 h / -50 - 30 °C / Inert atmosphere

7.2: 3 h / -78 - 20 °C / Inert atmosphere

8.1: triphenyl-arsane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

With pyridine; titanium(IV) isopropylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; ammonia borane; triphenyl-arsane; isopropylmagnesium chloride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: |Myers's Alkylation / 1.2: |Myers's Alkylation / 8.1: |Stille Cross Coupling;
DOI:10.1021/ja5043462