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

Base Information

Chemical Name:(E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-hept-2-en-1-ol
CAS No.:82919-27-5
Molecular Formula:C₂₂H₃₆O₃Si
Molecular Weight:376.612
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 12 articles about (E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-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:

: 82919-36-6
(E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-hept-2-enoic acid ethyl ester

: 82919-27-5
(E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-hept-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; at 0 ℃; for 0.5h; Yield given;
DOI:10.1021/ja00384a060

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 82919-27-5
(E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: diisobutylaluminium hydride / toluene / 0.33 h / 0 °C

3: CrO₃*2C₅H₅N / CH₂Cl₂ / 0.25 h / 0 °C

4: benzene / 16 h / Ambient temperature

5: diisobutylaluminium hydride / hexane / 0.5 h / 0 °C

With 2,6-dimethylpyridine; dipyridine chromium trioxide; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; benzene;
DOI:10.1021/ja00384a060

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 82919-27-5
(E)-(4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-hept-2-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: (c-C₅H₉)2BOTf, (2-C₃H₇)2NEt / CH₂Cl₂ / 2 h / 0 °C

2: conc. HF / acetonitrile / 3 h / Ambient temperature

3: ozone / CH₂Cl₂ / -78 °C

4: pyridine / hexane / 1 h / 50 °C

5: sodium m-periodate / methanol; H₂O / 5 h / Ambient temperature

6: diethyl ether / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

8: diisobutylaluminium hydride / toluene / 0.33 h / 0 °C

9: CrO₃*2C₅H₅N / CH₂Cl₂ / 0.25 h / 0 °C

10: benzene / 16 h / Ambient temperature

11: diisobutylaluminium hydride / hexane / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; dicyclopentylboron trifluoromethanesulfonate; hydrogen fluoride; dipyridine chromium trioxide; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1021/ja00384a060