(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

Base Information

Chemical Name:(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol
CAS No.:1352033-66-9
Molecular Formula:C₂₇H₃₂O₅
Molecular Weight:436.548
Hs Code.:

Synonyms:(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

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Chemical Property of (3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

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Technology Process of (3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

There total 8 articles about (3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol 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: 83.0%

: 1352033-65-8
(4S)-4-[4-(benzyloxy)-3-methoxyphenethyl]-2-(4-methoxyphenyl)-1,3-dioxane

: 1352033-66-9
(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

Guidance literature:: (4S)-4-[4-(benzyloxy)-3-methoxyphenethyl]-2-(4-methoxyphenyl)-1,3-dioxane; With diisobutylaluminium hydride; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;

With Rochelle's salt; In methanol; toluene; at 0 ℃; regioselective reaction; Saturated solution;
DOI:10.1016/j.tetasy.2011.09.012

Reference yield:

: 1352033-61-4
ethyl (E)-5-[4-(benzyloxy)-3-methoxyphenyl]-2-pentenoate

: 1352033-66-9
(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C / Inert atmosphere

1.2: Saturated solution

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 3 h / -24 °C / Molecular sieve; Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.2: 0 °C / Saturated solution

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Sharpless epoxidation;
DOI:10.1016/j.tetasy.2011.09.012

Reference yield:

: 1352033-62-5
(E)-5-[4-(benzyloxy)-3-methoxyphenyl]-2-penten-1-ol

: 1352033-66-9
(3S)-5-[4-(benzyloxy)-3-methoxyphenyl]-3-[(4-methoxybenzyl)oxy]pentan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 3 h / -24 °C / Molecular sieve; Inert atmosphere

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 0 °C / Saturated solution

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; 1.1: Sharpless epoxidation;
DOI:10.1016/j.tetasy.2011.09.012