(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

Base Information

Chemical Name:(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile
CAS No.:869385-05-7
Molecular Formula:C₃₅H₄₃NO₃Si
Molecular Weight:553.817
Hs Code.:

Synonyms:(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

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Chemical Property of (3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

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Technology Process of (3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

There total 10 articles about (3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile 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:

: (3S,4R)-4-Benzyloxy-3-methyl-5-oxo-pentanenitrile

: diethyl (6-((tert-butyldiphenylsilyl)oxy)-2-oxohexyl)phosphonate

: 869385-05-7
(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 - -20 ℃; for 2h;
DOI:10.1002/anie.200502296

Reference yield:

: 869385-16-0
(2S,3S,E)-3-(benzyloxy)-2-methyl-5-phenylpent-4-en-1-ol

: 869385-05-7
(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

2.1: 4.23 g / dimethylsulfoxide / 24 h / 50 °C

3.1: O₃ / methanol; CH₂Cl₂ / -78 °C

3.2: Me₂S / methanol; CH₂Cl₂ / 3 h / 20 °C

4.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

With dmap; sodium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 4.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/anie.200502296

Reference yield:

: (2R,4S,5S,E)-5-methyl-2-phenyl-4-styryl-1,3-dioxane

: 869385-05-7
(3S,4R,E)-4-benzyloxy-11-(tert-butyldiphenylsilyloxy)-3-methyl-7-oxoundec-5-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 76 percent / Dibal-H / CH₂Cl₂ / 36 h / -78 - -35 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: 4.23 g / dimethylsulfoxide / 24 h / 50 °C

4.1: O₃ / methanol; CH₂Cl₂ / -78 °C

4.2: Me₂S / methanol; CH₂Cl₂ / 3 h / 20 °C

5.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

With dmap; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 5.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/anie.200502296