(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

Base Information

Chemical Name:(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol
CAS No.:1452578-42-5
Molecular Formula:C₁₅H₁₉BrO₅
Molecular Weight:359.217
Hs Code.:

Synonyms:(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

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Chemical Property of (R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

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Technology Process of (R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

There total 5 articles about (R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol 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: 32.0%

: 1452578-39-0
(3aR,4S,6R,6aS)-4-(3-bromophenyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

: 1452578-42-5
(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 4h;
DOI:10.1039/c3ob41082j

Reference yield: 30.0%

: (3aS,6R,6aS)-4-(3-bromophenyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

: 1452578-42-5
(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

: 1452578-39-0
(3aR,4S,6R,6aS)-4-(3-bromophenyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

Guidance literature:: (3aS,6R,6aS)-4-(3-bromophenyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol; With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -40 ℃; for 1h; Inert atmosphere;

With potassium carbonate; In acetonitrile; at -40 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1039/c3ob41082j

Reference yield:

: 7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6
2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone

: 1452578-42-5
(R)-1-((3aS,4R,6S,6aR)-6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 1 h / -40 °C / Inert atmosphere

2.2: 1 h / -40 - 20 °C / Inert atmosphere

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; acetonitrile;
DOI:10.1039/c3ob41082j