(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

Base Information

Chemical Name:(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester
CAS No.:494834-79-6
Molecular Formula:C₃₃H₄₆O₅Si
Molecular Weight:550.811
Hs Code.:

Synonyms:(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

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Chemical Property of (E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

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Technology Process of (E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

There total 12 articles about (E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl 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: 65.0%

: 99285-25-3
(2E)-Hepta-2,6-dienoic acid chloride

: 494834-78-5
(Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol

: 494834-79-6
(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

Guidance literature:: With dmap; In dichloromethane;
DOI:10.1016/S0040-4039(02)02281-5

Reference yield:

: 119879-74-2
(R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propan-2-ol

: 494834-79-6
(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 22 °C

2.1: H₂ / Pd(OH)2 / ethyl acetate / 22 °C

3.1: COCl₂; DMSO; Et₃N / CH₂Cl₂ / -78 - 22 °C

4.1: TiCl₄ / CH₂Cl₂ / -78 °C

4.2: 79 percent / TFA / CH₂Cl₂ / 20 °C

5.1: NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

6.1: aq. camphorsulfonic acid / tetrahydrofuran / Heating

7.1: LiBH₄ / H₂O; tetrahydrofuran / 22 °C

8.1: DMAP / CH₂Cl₂ / 22 °C

With dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; camphor-10-sulfonic acid; hydrogen; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 3.1: Swern oxidation / 5.1: Luche reduction / 6.1: Ferrier rearrangement;
DOI:10.1021/ja048779q

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 494834-79-6
(E)-Hepta-2,6-dienoic acid (Z)-(4R,5S,6S)-7-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-6-methoxy-2,4-dimethyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: imidazole / dimethylformamide / 22 °C

2.1: NaH / tetrahydrofuran / 22 °C

3.1: H₂ / Pd(OH)2 / ethyl acetate / 22 °C

4.1: COCl₂; DMSO; Et₃N / CH₂Cl₂ / -78 - 22 °C

5.1: TiCl₄ / CH₂Cl₂ / -78 °C

5.2: 79 percent / TFA / CH₂Cl₂ / 20 °C

6.1: NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

7.1: aq. camphorsulfonic acid / tetrahydrofuran / Heating

8.1: LiBH₄ / H₂O; tetrahydrofuran / 22 °C

9.1: DMAP / CH₂Cl₂ / 22 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; camphor-10-sulfonic acid; hydrogen; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 4.1: Swern oxidation / 6.1: Luche reduction / 7.1: Ferrier rearrangement;
DOI:10.1021/ja048779q