(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

Base Information

Chemical Name:(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester
CAS No.:791131-48-1
Molecular Formula:C₂₈H₄₀O₇
Molecular Weight:488.621
Hs Code.:

Synonyms:(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

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Chemical Property of (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

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Technology Process of (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

There total 7 articles about (E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl 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:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 791131-48-1
(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / NaH / tetrahydrofuran / 2 h / 0 °C

2: AD-mix-β; MsNH2 / H2O; 2-methyl-propan-2-ol / 40 h / 0 °C

3: 99 percent / pTsOH*H₂O / 24 h / 20 °C

4: 91 percent / BuLi / tetrahydrofuran / 48 h / Heating

5: 65 percent / NaOH / aq. ethanol / 2 h / Heating

6: 63 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; sodium hydroxide; n-butyllithium; methanesulfonamide; AD-mix-β; sodium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation / 4: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol048396x

Reference yield:

: 791131-42-5
(E)-6-(4-Methoxy-benzyloxy)-3-methyl-hex-3-en-2-one

: 791131-48-1
(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: AD-mix-β; MsNH2 / H2O; 2-methyl-propan-2-ol / 40 h / 0 °C

2: 99 percent / pTsOH*H₂O / 24 h / 20 °C

3: 91 percent / BuLi / tetrahydrofuran / 48 h / Heating

4: 65 percent / NaOH / aq. ethanol / 2 h / Heating

5: 63 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; sodium hydroxide; n-butyllithium; methanesulfonamide; AD-mix-β; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 3: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol048396x

Reference yield:

: 791131-37-8
(3S)-5-(tert-butyldimethylsilanyloxymethyl)-3-methylhex-5-en-2-one

: 791131-48-1
(E)-3-{(4R,5R)-5-[2-(4-Methoxy-benzyloxy)-ethyl]-2,2,4-trimethyl-[1,3]dioxolan-4-yl}-but-2-enoic acid (S)-4-methyl-2-methylene-5-oxo-hexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 20 °C

2: 63 percent / DCC; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol048396x