(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

Base Information

Chemical Name:(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate
CAS No.:1393927-33-7
Molecular Formula:C₂₉H₄₆O₄Si₂
Molecular Weight:514.853
Hs Code.:

Synonyms:(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

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Chemical Property of (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

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Technology Process of (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

There total 4 articles about (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate 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: 87.0%

: 1393927-31-5
(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxypentan-2-yl acetate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1393927-33-7
(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

Guidance literature:: (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxypentan-2-yl acetate; With 1H-imidazole; dmap; In dichloromethane; at 0 ℃; for 0.333333h;

tert-butylchlorodiphenylsilane; In dichloromethane; at 0 - 20 ℃; for 8h;
DOI:10.1002/hlca.201100512

Reference yield:

: 1393927-30-4
(2R,4S)-4,5-dihydroxypentan-2-yl acetate

: 1393927-33-7
(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C

2.1: 1H-imidazole; dmap / dichloromethane / 0.33 h / 0 °C

2.2: 8 h / 0 - 20 °C

With 1H-imidazole; dmap; In dichloromethane;
DOI:10.1002/hlca.201100512

Reference yield:

: 64584-92-5
(R)-pent-4-en-2-ol

: 1393927-33-7
(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-{[(tert-butyl)diphenylsilyl]oxy}pentan-2-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 0.25 h / 0 °C

1.2: 4 h / 20 °C

2.1: potassium osmate(VI) dihydrate; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 8 h / 0 °C

3.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C

4.1: 1H-imidazole; dmap / dichloromethane / 0.33 h / 0 °C

4.2: 8 h / 0 - 20 °C

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;
DOI:10.1002/hlca.201100512