ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

Base Information

Chemical Name:ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate
CAS No.:351386-58-8
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

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Chemical Property of ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

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Technology Process of ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

There total 6 articles about ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate 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: 61.0%

: 351386-50-0
ethyl (4S)-(2Z)-4-benzyloxy-3-(diethylphosphoryl)-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-2,6-octadienoate

: 13170-43-9
(trimethylsilyl)methylmagnesium chloride

: 351386-58-8
ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

: ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[2-(trimethylsilyl)ethyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

Guidance literature:: With bis(acetylacetonate)nickel(II); In diethyl ether; at 20 ℃; for 2h;
DOI:10.1039/b010101j

Reference yield:

: 351386-46-4
isopropyl (2S)-2-benzyloxy-5-methyl-4-[(-2-tetrahydropyranyloxy)methyl]-4-hexenoate

: 351386-58-8
ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hexamethyldisilazane; BuLi / hexane; tetrahydrofuran / 0.17 h / -70 °C

1.2: TMEDA / hexane; tetrahydrofuran / 0.67 h

2.1: tBuOK / tetrahydrofuran / 0.05 h / 20 °C

2.2: 51 percent / tetrahydrofuran / 0.33 h / 20 °C

3.1: 61 percent / Ni(acac)2 / diethyl ether / 2 h / 20 °C

With bis(acetylacetonate)nickel(II); n-butyllithium; potassium tert-butylate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1039/b010101j

Reference yield:

: 351386-44-2
isopropyl (2S)-2-hydroxy-5-methyl-4-[(2-tetrahydropyranyloxy)methyl]-4-hexenoate

: 351386-58-8
ethyl (4S)-(2Z)-4-benzyloxy-7-methyl-6-[(2-tetrahydropyranyloxy)methyl]-3-[(trimethylsilyl)methyl]-2,6-octadienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / tBuOK; Bu₄NI / tetrahydrofuran / 0.5 h / 20 °C

2.1: hexamethyldisilazane; BuLi / hexane; tetrahydrofuran / 0.17 h / -70 °C

2.2: TMEDA / hexane; tetrahydrofuran / 0.67 h

3.1: tBuOK / tetrahydrofuran / 0.05 h / 20 °C

3.2: 51 percent / tetrahydrofuran / 0.33 h / 20 °C

4.1: 61 percent / Ni(acac)2 / diethyl ether / 2 h / 20 °C

With bis(acetylacetonate)nickel(II); n-butyllithium; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1039/b010101j