(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

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Chemical Name:(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester
CAS No.:143521-59-9
Molecular Formula:C₃₀H₄₀O₅Si
Molecular Weight:508.73
Hs Code.:

Synonyms:(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

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Chemical Property of (E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

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Technology Process of (E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

There total 23 articles about (E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester 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: 81.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 143521-72-6
{(2R,4S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-acetaldehyde

: 143521-59-9
(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(00)01337-X

Reference yield: 78.0%

: (E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-hydroxy-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

: 143521-59-9
(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

Guidance literature:: With dipyridinium dichromate; In dichloromethane; for 7h;
DOI:10.1016/S0040-4039(00)74816-7

Reference yield:

: 5694-95-1
2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

: 143521-59-9
(E)-4-{(2R,4R)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-oxo-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran

1.2: 76 percent / Bu₄NI

2.1: 97 percent / Dess-Martin periodinane

3.1: 83 percent / Bu₂BOTf / CH₂Cl₂

4.1: 85 percent / LiBH₄ / tetrahydrofuran

5.1: 99 percent / imidazole / dimethylformamide

6.1: 84 percent / EDC / CH₂Cl₂

7.1: 99 percent / FeCl₃; SiO₂ / CHCl₃

8.1: 91 percent / NaH / tetrahydrofuran / 0 °C

9.1: 98 percent / H₂ / Pd(OH)2-C / ethyl acetate

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂

11.1: 81 percent / BuLi / tetrahydrofuran / 20 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; hydrogen; silica gel; iron(III) chloride; sodium hydride; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 2.1: Oxidation / 3.1: Metallation / 4.1: Reduction / 5.1: Substitution / 6.1: Acylation / 7.1: Ring cleavage / 8.1: Cyclization / 9.1: Catalytic hydrogenation / 10.1: Oxidation / 11.1: Wadsworth-Emmons reaction;
DOI:10.1016/S0040-4039(00)01337-X