(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

Base Information

Chemical Name:(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate
CAS No.:1374407-51-8
Molecular Formula:C₂₇H₃₆O₅Si
Molecular Weight:468.665
Hs Code.:

Synonyms:(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

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Chemical Property of (2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

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Technology Process of (2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

There total 20 articles about (2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl 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: 60.0%

: 1374407-56-3
(2R,3R,4R)-4-hydroxy-2-methyl-4-vinyltetrahydro-3-furanyl acetate

: 143264-39-5
tert-butyl{[(1S)-1-methyl-2-propenyl]oxy}diphenylsilane

: 1374407-52-9
(2R,3R,4R)-4-{(E)-2-[(3R,4R,5R)-4-(acetyloxy)-3-hydroxy-5-methyltetrahydro-3-furanyl]-1-ethenyl}-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

: 1374407-51-8
(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In toluene; for 1h; Reflux; Inert atmosphere;
DOI:10.1002/ejoc.201101211

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1374407-51-8
(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C

3.1: potassium tert-butylate / tetrahydrofuran / 3 h / -5 °C

3.2: 3 h / 20 °C

4.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / Reflux; Inert atmosphere

With 1H-imidazole; Hoveyda-Grubbs catalyst second generation; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; 3.1: Wittig reaction / 3.2: Wittig reaction;
DOI:10.1002/ejoc.201101211

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 1374407-51-8
(2R,3R,4R)-4-(E,3S)-3-{[1-tert-butyl-diphenylsilyl]oxy}-1-butenyl-4-hydroxy-2-methyltetrahydro-3-furanyl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 3 h / -5 °C

1.2: 3 h / 20 °C

2.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / Reflux; Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; potassium tert-butylate; In tetrahydrofuran; toluene; 1.1: Wittig reaction / 1.2: Wittig reaction;
DOI:10.1002/ejoc.201101211