5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

Base Information

Chemical Name:5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester
CAS No.:879873-92-4
Molecular Formula:C₂₃H₃₄O₆
Molecular Weight:406.519
Hs Code.:

Synonyms:5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

There total 14 articles about 5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-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: 97.0%

: 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

: 879873-92-4
5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

Guidance literature:: With (1S)-10-camphorsulfonic acid; water; In methanol; at 20 ℃; for 2.5h;
DOI:10.1021/ol052851n

Reference yield:

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

: 879873-92-4
5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

7.1: 97 percent / 10-camphorsulfonic acid; H₂O / methanol / 2.5 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; 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

: 879873-92-4
5,7-dihydroxy-9-(4-methoxybenzyloxy)-4-methyl-9-(2-methylcyclopropyl)non-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: 97 percent / 10-camphorsulfonic acid; H₂O / methanol / 2.5 h / 20 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; 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