(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

Base Information

Chemical Name:(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane
CAS No.:426841-73-8
Molecular Formula:C₂₂H₂₈O₆
Molecular Weight:388.461
Hs Code.:

Synonyms:(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

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Chemical Property of (4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

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Technology Process of (4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

There total 7 articles about (4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane 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:

: 291506-89-3
(3R,5S)-6-benzyloxy-3,5-dihydroxyhexanoic acid isopropyl ester

: 426841-73-8
(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h / 23 °C

2: 91 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

4: 156 mg / CHCl₃ / 15 h / Heating

5: diethyl ether / 0.5 h / 0 °C

6: 146 mg / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

With dmap; oxalyl dichloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In diethyl ether; dichloromethane; chloroform; ethyl acetate; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1055/s-2002-20037

Reference yield:

: 108-24-7
acetic anhydride

: [(4R,6S)-6-((E)-3-Hydroxy-penta-1,4-dienyl)-2-phenyl-[1,3]dioxan-4-yl]-acetic acid isopropyl ester

: 426841-73-8
(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1055/s-2002-20037

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 426841-73-8
(4S,6R)-4-[(1E)-3-acetyloxypenta-1,4-dienyl]-6-isopropoxycarbonylmethyl-2-phenyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 23 °C

3: 156 mg / CHCl₃ / 15 h / Heating

4: diethyl ether / 0.5 h / 0 °C

5: 146 mg / Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 °C

With dmap; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; chloroform; 2: Swern oxidation / 3: Wittig olefination;
DOI:10.1055/s-2002-20037