(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester
CAS No.:879873-91-3
Molecular Formula:C₂₆H₃₈O₆
Molecular Weight:446.584
Hs Code.:

Synonyms:(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

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Chemical Property of (E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

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Technology Process of (E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

There total 14 articles about (E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic 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: 89.0%

: 879873-90-2
2-{6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-2,2-dimethyl[1,3]dioxan-4-yl}propionaldehyde

: 5927-18-4
trimethyl phosphonoacetate

: 879873-91-3
(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 0 - 20 ℃; for 5h;
DOI:10.1021/ol052851n

Reference yield:

: 879873-85-5
4-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)butan-2-one

: 879873-91-3
(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: iPr₂NEt; Bu₂BOTf / diethyl ether / 2 h / -78 °C

1.2: 93 percent / H₂O₂ / ethanol; methanol / 1 h / 20 °C / pH 7

2.1: 95 percent / Me₄NB(OAc)3H; AcOH / acetonitrile / 48 h / -20 °C

3.1: 83 percent / PPTS / CH₂Cl₂ / 5 h / 20 °C

4.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6.1: 89 percent / iPr₂NEt; LiCl / acetonitrile / 5 h / 0 - 20 °C

With di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 1.1: aldol reaction / 5.1: Dess-Martin oxidation / 6.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol052851n

Reference yield:

: 879873-84-4
1-Methoxy-4-[(S)-3-methyl-1-((1R,2R)-2-methyl-cyclopropyl)-but-3-enyloxymethyl]-benzene

: 879873-91-3
(E)-(S)-4-{(4S,6R)-6-[(S)-2-(4-Methoxy-benzyloxy)-2-((1R,2R)-2-methyl-cyclopropyl)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine; O₃ / methanol / -78 °C

1.2: 96 percent / Me₂S / methanol / 4 h / -78 - 20 °C

2.1: iPr₂NEt; Bu₂BOTf / diethyl ether / 2 h / -78 °C

2.2: 93 percent / H₂O₂ / ethanol; methanol / 1 h / 20 °C / pH 7

3.1: 95 percent / Me₄NB(OAc)3H; AcOH / acetonitrile / 48 h / -20 °C

4.1: 83 percent / PPTS / CH₂Cl₂ / 5 h / 20 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

6.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: 89 percent / iPr₂NEt; LiCl / acetonitrile / 5 h / 0 - 20 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 2.1: aldol reaction / 6.1: Dess-Martin oxidation / 7.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol052851n