(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Base Information

Chemical Name:(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol
CAS No.:157430-97-2
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

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Chemical Property of (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

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Technology Process of (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

There total 7 articles about (E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-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: 100.0%

: 179944-92-4
(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-enoic acid ethyl ester

: 157430-97-2
(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jo9606113

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 157430-97-2
(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

4: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

With 2,6-dimethylpyridine; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo9606113

Reference yield:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 157430-97-2
(E)-(4R,5S,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 1.) trimethylaluminum / 1.) THF, toluene, 0 deg C -> room temperature, 2.) THF, toluene, CH₂Cl₂, -10 -> 0 deg C

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

5: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

6: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; trimethylaluminum; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo9606113