(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

Base Information

Chemical Name:(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol
CAS No.:204327-30-0
Molecular Formula:C₂₃H₄₀O₅Si
Molecular Weight:424.653
Hs Code.:

Synonyms:(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

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Chemical Property of (E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

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Technology Process of (E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

There total 8 articles about (E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol 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: 94.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 204327-29-7
(E)-(3S,4S,7R)-7-Benzyloxy-4-methoxymethoxy-oct-5-ene-1,3-diol

: 204327-30-0
(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 4h; Ambient temperature;
DOI:10.1021/jo972187r

Reference yield:

: 100-39-0
benzyl bromide

: 204327-30-0
(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / Ag₂O / diethyl ether / Heating

2: 96 percent / DIBAL / diethyl ether; pentane; hexane / 0.5 h / -78 °C

3: 1.) NaH / 1.) THF, -40 deg C, 40 min, 2.) THF, room temp., 20 h

4: DIBAL, ZnBr₂

5: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

6: 99 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Ambient temperature

7: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; zinc dibromide; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/jo972187r

Reference yield:

: 53346-05-7,41954-96-5,81445-44-5,81445-45-6
(R)-2-benzyloxypropanal

: 204327-30-0
(E)-(3S,4S,7R)-7-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-oct-5-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, -40 deg C, 40 min, 2.) THF, room temp., 20 h

2: DIBAL, ZnBr₂

3: 90 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

4: 99 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Ambient temperature

5: 94 percent / imidazole / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; zinc dibromide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo972187r