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

Base Information

Chemical Name:(Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol
CAS No.:494834-78-5
Molecular Formula:C₂₆H₃₈O₄Si
Molecular Weight:442.671
Hs Code.:

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

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Chemical Property of (Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol

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Technology Process of (Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol

There total 16 articles about (Z)-(4R,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-ene-1,5-diol 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:

: 494834-77-4
6-[2-(tert-butyl-diphenyl-silanyloxy)-1-methoxy-ethyl]-3,5-dimethyl-5,6-dihydro-2H-pyran-2-ol

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

Guidance literature:: With lithium borohydride; In tetrahydrofuran; water;
DOI:10.1016/S0040-4039(02)02281-5

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 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

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; 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