Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

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Chemical Name:Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester
CAS No.:474005-81-7
Molecular Formula:C₂₇H₃₆O₅Si
Molecular Weight:468.665
Hs Code.:

Synonyms:Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

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Chemical Property of Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

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Technology Process of Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

There total 7 articles about Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl 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: 80.0%

: 474005-80-6
Acetic acid (E)-3-[(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

: 474005-81-7
Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;
DOI:10.1021/ol026504e

Reference yield:

: 474005-77-1
(2E,7E)-(4S,6R)-Nona-2,7-diene-1,4,6,9-tetraol

: 474005-81-7
Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 84 percent / 2,6-lutidine / acetonitrile / 3 h / -20 °C

2.1: 81 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / tetrahydrofuran / 20 °C

3.1: 78 percent / camphorsulfonic acid / CH₂Cl₂ / -20 °C

4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / -20 °C

4.2: 81 percent / NaBO₃ / tetrahydrofuran; H₂O / 0.5 h

5.1: 96 percent / imidazole / dimethylformamide / 20 °C

6.1: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; camphor-10-sulfonic acid; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol026504e

Reference yield:

: 474005-76-0
(2E,7E)-(4R,6S)-4,6-Diacetoxy-nona-2,7-dienedioic acid diethyl ester

: 474005-81-7
Acetic acid (E)-3-{(2S,4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-2-yl}-allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: DIBAL / diethyl ether; toluene / -78 - 0 °C

1.2: Rochelle's salt / diethyl ether; toluene; methanol / 1 h

1.3: 85 percent / MgSO₄ / diethyl ether; toluene; methanol / 0.5 h

2.1: 84 percent / 2,6-lutidine / acetonitrile / 3 h / -20 °C

3.1: 81 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / tetrahydrofuran / 20 °C

4.1: 78 percent / camphorsulfonic acid / CH₂Cl₂ / -20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / -20 °C

5.2: 81 percent / NaBO₃ / tetrahydrofuran; H₂O / 0.5 h

6.1: 96 percent / imidazole / dimethylformamide / 20 °C

7.1: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; camphor-10-sulfonic acid; diisobutylaluminium hydride; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol026504e