(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

Base Information

Chemical Name:(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate
CAS No.:1123785-30-7
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

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Chemical Property of (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

Chemical Property:

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Technology Process of (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

There total 8 articles about (4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate 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:

: 1123785-66-9
C₂₂H₃₈O₃Si

: (4R,5R,8S,Z)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

: 1123785-30-7
(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

Guidance literature:: With ethyl (triphenylphosphoranylidene)acetate; In benzene; at 20 ℃; for 24h; Overall yield = 2.2 g;
DOI:10.1016/j.tetasy.2012.07.006

Reference yield:

: 1123785-66-9
C₂₂H₃₈O₃Si

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: (4R,5R,8S,Z)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

: 1123785-30-7
(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

Guidance literature:: In benzene; at 20 ℃; for 10h; optical yield given as %de;
DOI:10.1016/j.tetlet.2008.11.088

Reference yield:

: 5673-98-3,63501-27-9,88080-30-2,63501-26-8
(S)-(-)-2-methyl-4-penten-1-ol

: 1123785-30-7
(4R,5R,8S,E)-ethyl 9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

1.2: 2 h / 0 - 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 °C

2.2: 16 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

4.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C

4.2: 0.5 h / 0 °C

4.3: 1 h / 0 °C

5.1: 2,6-dimethylpyridine / 0.5 h / 0 °C

6.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 6 h / 20 °C

7.1: dipyridinium dichromate / dichloromethane / 20 °C

8.1: ethyl (triphenylphosphoranylidene)acetate / benzene / 24 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; dipyridinium dichromate; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; Dess-Martin periodane; ethyl (triphenylphosphoranylidene)acetate; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; benzene; 4.1: |Evans Aldol Reaction / 4.2: |Evans Aldol Reaction;
DOI:10.1016/j.tetasy.2012.07.006