(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

Base Information

Chemical Name:(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol
CAS No.:334972-48-4
Molecular Formula:C₂₁H₃₀O₄
Molecular Weight:346.467
Hs Code.:

Synonyms:(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

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Chemical Property of (1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

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Technology Process of (1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

There total 10 articles about (1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol 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: 59.0%

: 334972-47-3
(R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal

: 334972-48-4
(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

Guidance literature:: With dimethylaluminum chloride; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4039(00)02179-1

Reference yield:

: 127102-61-8
(S)-hex-5-ene-1,2-diol

: 334972-48-4
(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 percent / Et₃N; DMAP / CH₂Cl₂

2.1: 90 percent / TfOH / diethyl ether

3.1: OsO₄; NMO / 2-methyl-propan-2-ol; acetone; H₂O

3.2: 98 percent / NaIO₄; SiO₂ / H₂O; CH₂Cl₂

4.1: 93 percent / t-BuOH / toluene / -20 °C

5.1: 99 percent / PPTS / methanol

6.1: 68 percent / t-BuOK / tetrahydrofuran / -10 - -4 °C

7.1: 98 percent / DIBAL / toluene / -78 °C

8.1: 59 percent / Me₂AlCl / CH₂Cl₂ / 0 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; potassium tert-butylate; dimethylaluminum chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 4.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/S0040-4039(00)02179-1

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 334972-48-4
(1S,2S,5R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-5-(1-methylethenyl)cyclopentanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / TfOH / diethyl ether

2.1: OsO₄; NMO / 2-methyl-propan-2-ol; acetone; H₂O

2.2: 98 percent / NaIO₄; SiO₂ / H₂O; CH₂Cl₂

3.1: 93 percent / t-BuOH / toluene / -20 °C

4.1: 99 percent / PPTS / methanol

5.1: 68 percent / t-BuOK / tetrahydrofuran / -10 - -4 °C

6.1: 98 percent / DIBAL / toluene / -78 °C

7.1: 59 percent / Me₂AlCl / CH₂Cl₂ / 0 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; potassium tert-butylate; dimethylaluminum chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 3.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/S0040-4039(00)02179-1