(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole
CAS No.:1313604-14-6
Molecular Formula:C₂₃H₂₈O₅
Molecular Weight:384.472
Hs Code.:

Synonyms:(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

There total 6 articles about (3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole 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: 90.0%

: (3aR,5S)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)vinyl}tetrahydrofurano[2,3-d][1,3]dioxole

: 1313604-14-6
(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

Guidance literature:: With Wilkinson's catalyst; hydrogen; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 6h; under 760.051 Torr;
DOI:10.1016/j.tetlet.2011.04.097

Reference yield: 70.0%

: C₁₆H₂₂O₅

: 100-39-0
benzyl bromide

: 1313604-14-6
(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

Guidance literature:: With potassium carbonate; In acetone;
DOI:10.1002/ejoc.201801211

Reference yield:

: 281670-28-8
(3aR,5S,6aR)-5-Bromomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

: 1313604-14-6
(3aR,5R)-2,2-dimethyl-5-{2-(4-benzyloxy-3-methoxyphenyl)ethyl}tetrahydrofurano[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: copper(ll) sulfate pentahydrate / methanol; water / 1.5 h / 60 °C

3.1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol

4.1: potassium carbonate / acetone

With copper(ll) sulfate pentahydrate; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium hydride; potassium carbonate; In methanol; ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1002/ejoc.201801211