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

Base Information

Chemical Name:(2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-4-methyl-6-oxocyclohexanecarboxylate
CAS No.:869385-09-1
Molecular Formula:C₄₁H₅₄O₆Si
Molecular Weight:670.962
Hs Code.:

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

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

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

There total 17 articles about (2S,3R,4S)-tert-butyl 3-benzyloxy-2-(6-(tert-butyldiphenylsilyloxy)-2-oxohexyl)-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: 96.0%

: 869385-08-0
(5S,6R,E)-tert-butyl 6-benzyloxy-13-(tert-butyldiphenylsilyloxy)-5-methyl-3,9-dioxotridec-7-enoate

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

Guidance literature:: With caesium carbonate; In ethanol; at -78 - 0 ℃;
DOI:10.1002/anie.200502296

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 7.1 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

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

3.1: 5.25 g / imidazole / dimethylformamide / 30 h / 20 °C

4.1: 83 percent / Dibal-H / CH₂Cl₂ / 1.5 h / -78 - -50 °C

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

6.1: PPTS / ethanol / 1.25 h / 20 °C

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

7.1: 96 percent / Cs₂CO₃ / ethanol / -78 - 0 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; diisobutylaluminium hydride; caesium carbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Horner-Wadsworth-Emmons reaction / 6.2: Dess-Martin oxidation;
DOI:10.1002/anie.200502296

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 10 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

With 1H-imidazole; dmap; 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; 4.1: Horner-Wadsworth-Emmons reaction / 9.2: Dess-Martin oxidation;
DOI:10.1002/anie.200502296