{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

Base Information

Chemical Name:{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester
CAS No.:879873-93-5
Molecular Formula:C₂₃H₃₄O₆
Molecular Weight:406.519
Hs Code.:

Synonyms:{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

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Chemical Property of {4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

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Technology Process of {4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

There total 15 articles about {4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic 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: 82.0%

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

: {4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

: 879873-93-5
{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h; Title compound not separated from byproducts;
DOI:10.1021/ol052851n

Reference yield:

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

: 879873-93-5
{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: 82 percent / NaH / tetrahydrofuran / 4 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; 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

: 879873-93-5
{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

9.1: 82 percent / NaH / tetrahydrofuran / 4 h / 20 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; 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