(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

Base Information

Chemical Name:(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide
CAS No.:908297-39-2
Molecular Formula:C₃₁H₄₆O₃Si₂
Molecular Weight:522.875
Hs Code.:

Synonyms:(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

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Chemical Property of (2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

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Technology Process of (2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

There total 5 articles about (2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide 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: 39.0%

: 908297-38-1
(4R,5S)-5-(t-butyldiphenylsilyloxy)-4-heptanolide

: 120950-81-4
1-iodo-5-trimethylsilyl-3-pentene

: 908297-39-2
(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

: (2S,4R,5R)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

Guidance literature:: (4R,5S)-5-(t-butyldiphenylsilyloxy)-4-heptanolide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -65 ℃; for 0.25h;

1-iodo-5-trimethylsilyl-3-pentene; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
DOI:10.1021/jo0608927

Reference yield:

: 865487-10-1
(4R,5R)-5-(t-butyldiphenylsolyloxy)-4-heptanolide

: 908297-39-2
(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / TBAF; HF / tetrahydrofuran; H₂O / 72 h / pH 7.0

2.1: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 16 h / cooling

3.1: 0.394 mg / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

4.1: 0.572 g / imidazole / dimethylformamide / 17 h

5.1: LDA / tetrahydrofuran; hexane / 0.25 h / -65 °C

5.2: 39 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; hydrogen fluoride; tetrabutyl ammonium fluoride; potassium carbonate; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0608927

Reference yield:

: 908297-46-1
4-Nitro-benzoic acid (S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-propyl ester

: 908297-39-2
(2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-[(Z)-5-trimethylsilyl-3-pentenyl]-4-heptanolide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 0.394 mg / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

2.1: 0.572 g / imidazole / dimethylformamide / 17 h

3.1: LDA / tetrahydrofuran; hexane / 0.25 h / -65 °C

3.2: 39 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;
DOI:10.1021/jo0608927