(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

Base Information

Chemical Name:(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate
CAS No.:1549824-43-2
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

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Chemical Property of (4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

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Technology Process of (4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

There total 8 articles about (4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate 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: 68.0%

: 201230-82-2
carbon monoxide

: 1549824-37-4
(4S,5S,Z)-ethyl 8-iodo-4-methyl-5-(triisopropylsilyloxy)nona-2,8-dienoate

: 108-95-2,27073-41-2
phenol

: 1549824-43-2
(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 50 ℃; for 7h;
DOI:10.1016/j.tetlet.2013.12.110

Reference yield: 68.0%

: 124-38-9,18923-20-1
carbon dioxide

: 1549824-37-4
(4S,5S,Z)-ethyl 8-iodo-4-methyl-5-(triisopropylsilyloxy)nona-2,8-dienoate

: 108-95-2,27073-41-2
phenol

: 1549824-43-2
(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

Guidance literature:: (4S,5S,Z)-ethyl 8-iodo-4-methyl-5-(triisopropylsilyloxy)nona-2,8-dienoate; phenol; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at 50 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tetlet.2013.12.110

Reference yield:

: 1549824-21-6
(2R,3S)-methyl 6-iodo-2-methyl-3-(triisopropylsilyloxy)hept-6-enoate

: 1549824-43-2
(4S,5S,Z)-1-ethyl-9-phenyl-4-methyl-8-methylene-5-(triisopropylsilyloxy)non-2-enedioate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

2.1: N-benzyl-trimethylammonium hydroxide / methanol; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 7 h / 50 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetlet.2013.12.110