tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

Base Information

Chemical Name:tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate
CAS No.:1605346-52-8
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

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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 tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

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Technology Process of tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

There total 5 articles about tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate 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: 78.0%

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 210702-67-3
(4S,5R)-4-[(benzyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

: 1605346-52-8
tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In dichloromethane; diastereoselective reaction; Reflux; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.02.004

Reference yield:

: 155934-55-7
(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 1605346-52-8
tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / Petroleum ether; tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux; Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; Petroleum ether;
DOI:10.1016/j.tetasy.2014.02.004

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 1605346-52-8
tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrogenchloride / water / 1 h / 60 °C

1.2: 1 h / 60 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

4.1: sodium hydride / Petroleum ether; tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

4.2: 16 h / 20 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux; Inert atmosphere

With hydrogenchloride; n-butyllithium; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; Petroleum ether;
DOI:10.1016/j.tetasy.2014.02.004