(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

Base Information

Chemical Name:(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate
CAS No.:1251537-19-5
Molecular Formula:C₃₇H₅₀O₄Si₂
Molecular Weight:614.973
Hs Code.:

Synonyms:(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

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Chemical Property of (5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

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Technology Process of (5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

There total 5 articles about (5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate 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:

: 1251537-14-0
(S)-isopropyl 5-hydroxyhept-6-ynoate

: C₂₇H₃₅IOSi₂

: 1251537-19-5
(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.03.035

Reference yield:

: 1251537-13-9
C₁₃H₂₄O₃Si

: 1251537-19-5
(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: ammonium chloride / tetrahydrofuran / 0.25 h / 0 °C

1.2: 2 h / 20 °C

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine / 16 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium chloride; diethylamine; In tetrahydrofuran; 2.1: Sonogashira coupling;
DOI:10.1016/j.tetlet.2011.03.035

Reference yield:

: 187085-44-5
7-(trimethylsilyl)-5-oxohept-6-ynoic acid

: 1251537-19-5
(5S,8E,10E,12R)-isopropyl 12-(tert-butyldiphenylsilyloxy)-5-hydroxy-15-(trimethylsilyl)pentadeca-8,10-dien-6,14-diynoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / 24 h / 65 °C

2.1: Noyori catalyst / isopropyl alcohol / 0.33 h / 20 °C

3.1: ammonium chloride / tetrahydrofuran / 0.25 h / 0 °C

3.2: 2 h / 20 °C

4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylamine / 16 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium chloride; toluene-4-sulfonic acid; diethylamine; In tetrahydrofuran; isopropyl alcohol; 4.1: Sonogashira coupling;
DOI:10.1016/j.tetlet.2011.03.035