(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

Base Information

Chemical Name:(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate
CAS No.:869385-10-4
Molecular Formula:C₄₄H₅₇NO₆Si
Molecular Weight:724.025
Hs Code.:

Synonyms:(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

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Chemical Property of (1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

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Technology Process of (1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

There total 17 articles about (1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate 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:

: 869385-09-1
(2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate

: 107-13-1,25014-41-9
acrylonitrile

: 869385-10-4
(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: With tetra(n-butyl)ammonium hydroxide; In acetonitrile; at 20 ℃; for 5h;
DOI:10.1002/anie.200502296

Reference yield:

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

: 869385-10-4
(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 11 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

5.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C

6.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C

7.1: 83 percent / Dibal-H / CH₂Cl₂ / 1.5 h / -78 - -50 °C

8.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C

9.1: PPTS / ethanol / 1.25 h / 20 °C

9.2: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

10.1: 96 percent / Cs₂CO₃ / ethanol / -78 - 0 °C

11.1: Bu₄NOH*30H₂O / acetonitrile / 5 h / 20 °C

With 1H-imidazole; dmap; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; caesium carbonate; ozone; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 4.1: Horner-Wadsworth-Emmons reaction / 9.2: Dess-Martin oxidation / 11.1: Michael addition;
DOI:10.1002/anie.200502296

Reference yield:

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

: 869385-10-4
(1R,2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-1-(2-cyanoethyl)-4-methyl-6-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 12 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

6.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C

7.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C

8.1: 83 percent / Dibal-H / CH₂Cl₂ / 1.5 h / -78 - -50 °C

9.1: LDA / tetrahydrofuran; hexane / 1.17 h / -78 - 0 °C

10.1: PPTS / ethanol / 1.25 h / 20 °C

10.2: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 20 °C

11.1: 96 percent / Cs₂CO₃ / ethanol / -78 - 0 °C

12.1: Bu₄NOH*30H₂O / acetonitrile / 5 h / 20 °C

With 1H-imidazole; dmap; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; caesium carbonate; ozone; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 5.1: Horner-Wadsworth-Emmons reaction / 10.2: Dess-Martin oxidation / 12.1: Michael addition;
DOI:10.1002/anie.200502296