(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

Base Information

Chemical Name:(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol
CAS No.:204776-60-3
Molecular Formula:C₂₃H₂₈O₆
Molecular Weight:400.472
Hs Code.:

Synonyms:(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

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Chemical Property of (R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

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Technology Process of (R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

There total 4 articles about (R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol 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: 81.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 35781-78-3
5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 204776-60-3
(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

Guidance literature:: 1-bromo-4-methoxy-benzene; With iodine; magnesium; In tetrahydrofuran; Reflux;

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose; With copper(l) cyanide; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; regioselective reaction; Inert atmosphere;
DOI:10.1055/s-0035-1561365

Reference yield: 81.0%

: 13139-86-1
4-methoxyphenyl magnesium bromide

: 35781-78-3
5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 204776-60-3
(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1016/S0957-4166(98)00017-2

Reference yield:

: 23313-03-3
(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

: 204776-60-3
(R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(4-methoxyphenyl)ethanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / methanol / 0.5 h / 20 °C

2.1: magnesium; iodine / tetrahydrofuran / Reflux

2.2: 2.5 h / 0 - 20 °C / Inert atmosphere

With iodine; potassium carbonate; magnesium; In tetrahydrofuran; methanol; 2.1: |Grignard Reaction / 2.2: |Grignard Reaction;
DOI:10.1055/s-0035-1561365