(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

Base Information

Chemical Name:(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester
CAS No.:596095-56-6
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

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Chemical Property of (2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

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Technology Process of (2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

There total 8 articles about (2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester 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: 65.0%

: 2689-62-5
(1-methoxy-1-oxopropan-2-yl)triphenylphosphonium bromide

: (E)-(4R,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethyl-pent-2-enal

: 596095-56-6
(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(03)01173-0

Reference yield:

: 88406-01-3
2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol

: 596095-56-6
(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 66 percent / NaH; TBAI / dimethylformamide / 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 80 percent / PPh₃ / -25 °C

3.1: 70 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

4.1: 94 percent / DIBAL-H / hexane / -78 °C

5.1: 85 percent / DMP / CH₂Cl₂ / 0 °C

6.1: 65 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; phthalic acid dimethyl ester; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; ozone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Wittig reaction;
DOI:10.1016/S0040-4039(03)01173-0

Reference yield:

: 109121-41-7
(R)-4-((1S,2R)-1-benzyloxy-2-methylbut-3-enyl)-2,2-dimethyl-[1,3]dioxolane

: 596095-56-6
(2E,4E)-(6R,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 80 percent / PPh₃ / -25 °C

2.1: 70 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

3.1: 94 percent / DIBAL-H / hexane / -78 °C

4.1: 85 percent / DMP / CH₂Cl₂ / 0 °C

5.1: 65 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; phthalic acid dimethyl ester; diisobutylaluminium hydride; ozone; In tetrahydrofuran; hexane; dichloromethane; 5.1: Wittig reaction;
DOI:10.1016/S0040-4039(03)01173-0