(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

Base Information

Chemical Name:(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one
CAS No.:1357931-50-0
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

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Chemical Property of (S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

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Technology Process of (S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

There total 3 articles about (S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one 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%

: 1357931-49-7
(S)-1-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]pent-4-en-2-ol

: 78-94-4,25038-87-3
methyl vinyl ketone

: 1357931-50-0
(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In dichloromethane; for 2h; Inert atmosphere; Reflux;
DOI:10.1021/ja208668u

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 1357931-50-0
(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 4 h / Inert atmosphere; Reflux

2: 2,6-dimethylpyridine / dichloromethane / 0.17 h / -78 °C / Inert atmosphere; Reflux

3: bismuth (III) nitrate pentahydrate / dichloromethane / 20 °C

4: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide / dichloromethane / 48 h / -15 - 20 °C / Inert atmosphere; Darkness

5: Hoveyda-Grubbs catalyst second generation / dichloromethane / 2 h / Inert atmosphere; Reflux

With 2,6-dimethylpyridine; titanium(IV) isopropylate; Hoveyda-Grubbs catalyst second generation; bismuth (III) nitrate pentahydrate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide; In dichloromethane;
DOI:10.1021/ja208668u

Reference yield:

: 1357931-48-6
2-[(2R,4S,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]acetaldehyde

: 1357931-50-0
(S,E)-7-[(2R,4R,6R)-6-(benzyloxymethyl)-2-methyl-1,3-dioxan-4-yl]-6-hydroxyhept-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide / dichloromethane / 48 h / -15 - 20 °C / Inert atmosphere; Darkness

2: Hoveyda-Grubbs catalyst second generation / dichloromethane / 2 h / Inert atmosphere; Reflux

With titanium(IV) isopropylate; Hoveyda-Grubbs catalyst second generation; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; silver(l) oxide; In dichloromethane;
DOI:10.1021/ja208668u