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

Base Information

Chemical Name:(E)-(4S,5R,6R,7R)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol
CAS No.:131589-40-7
Molecular Formula:C₂₅H₄₄O₃Si
Molecular Weight:420.708
Hs Code.:

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

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

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

There total 10 articles about (E)-(4S,5R,6R,7R)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-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: 95.0%

: 131589-25-8
methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

: 131589-40-7
(E)-(4S,5R,6R,7R)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -10 ℃; for 0.25h;
DOI:10.1021/ja00003a026

Reference yield:

: 123219-41-0
(2R,3S,4R,5R)-3-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanal

: 131589-40-7
(E)-(4S,5R,6R,7R)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / tetrahydrofuran / 72 h / 22 °C

2: 95 percent / DIBAL / toluene / 0.25 h / -10 °C

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1021/ja00003a026

Reference yield:

: 100-39-0
benzyl bromide

: 131589-40-7
(E)-(4S,5R,6R,7R)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) from -50 deg C to RT, overnight

2: 96 percent / formic acid / diethyl ether / 22 °C

3: oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4: 62 percent / diethyl ether / 2 h / 22 °C

5: 97 percent / imidazole / dimethylformamide / 48 h / 60 °C

6: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

7: 95 percent / tetrahydrofuran / 72 h / 22 °C

8: 95 percent / DIBAL / toluene / 0.25 h / -10 °C

With 1H-imidazole; formic acid; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00003a026