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

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Chemical Name:(R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal
CAS No.:334972-47-3
Molecular Formula:C₂₁H₃₀O₄
Molecular Weight:346.467
Hs Code.:

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

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Chemical Property of (R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal

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Technology Process of (R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal

There total 8 articles about (R)-2-[(2'R,5'S)-5'-(4-Methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enal 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: 98.0%

: 334972-46-2
Ethyl (R)-2-[(2'R,5'S)-5'-(4-methoxybenzyloxy)tetrahydropyran-2'-yl]-6-methylhept-5-enoate

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

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃;
DOI:10.1016/S0040-4039(00)02179-1

Reference yield:

: Ethyl (S)-7-hydroxy-6-(4-methoxybenzyloxy)-2-(4'-methylpent-3'-enyl)hept-2-enoate

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

Guidance literature:: Multi-step reaction with 2 steps

1: t-BuOK / tetrahydrofuran / 18 h / 4 °C

2: 98 percent / DIBAL-H / toluene / 3 h / -78 °C

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; toluene; 1: oxy-Michael-type cyclization;
DOI:10.1039/b100777g

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; potassium tert-butylate; 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