(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

Base Information

Chemical Name:(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol
CAS No.:1422347-12-3
Molecular Formula:C₂₇H₃₈O₂Si
Molecular Weight:422.683
Hs Code.:

Synonyms:(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

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Chemical Property of (4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

Chemical Property:

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Technology Process of (4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

There total 9 articles about (4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-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:

: 1422347-17-8
(S,E)-ethyl 6-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-2-enoate

: 106-95-6
allyl bromide

: 1422347-12-3
(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

: 1422347-13-4
(4R,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

Guidance literature:: With ammonium chloride; zinc; In tetrahydrofuran; at 0 ℃; for 3.25h; Overall yield = 1.8 g;
DOI:10.1016/j.tetlet.2012.11.015

Reference yield:

: 1422347-13-4
(4R,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

: 1422347-12-3
(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 10 - 20 °C

2: potassium carbonate; methanol / 0.5 h

With methanol; di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; 1: |Mitsunobu Displacement;
DOI:10.1016/j.tetlet.2012.11.015

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 1422347-12-3
(4S,7S,E)-9-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 11 steps

1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C

2: dichloromethane / 2 h / 20 °C

3: diisobutylaluminium hydride / dichloromethane / 2 h / -78 - 20 °C

4: diethyl (2S,3S)-tartrate; tert.-butylhydroperoxide; titanium(IV)isopropoxide / dichloromethane / 8 h / -30 °C

5: toluene; dichloromethane / 2 h / 0 °C / Inert atmosphere

6: sodium periodate / tetrahydrofuran; water / 2 h / 0 - 20 °C

7: benzene / 3 h / 20 °C

8: diisobutylaluminium hydride / toluene; dichloromethane / 2.33 h / -78 - 20 °C / Inert atmosphere

9: zinc; ammonium chloride / tetrahydrofuran / 3.25 h / 0 °C

10: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 10 - 20 °C

11: potassium carbonate; methanol / 0.5 h

With methanol; tert.-butylhydroperoxide; sodium periodate; dipyridinium dichromate; diethyl (2S,3S)-tartrate; di-isopropyl azodicarboxylate; titanium(IV)isopropoxide; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 4: |Sharpless Asymmetric Epoxidation / 7: |Wittig Olefination / 9: |Barbier Coupling Reaction / 10: |Mitsunobu Displacement;
DOI:10.1016/j.tetlet.2012.11.015