(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Base Information

Chemical Name:(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate
CAS No.:1452578-49-2
Molecular Formula:C₁₂H₁₃BrO₅
Molecular Weight:317.136
Hs Code.:

Synonyms:(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

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Chemical Property of (2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

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Technology Process of (2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

There total 6 articles about (2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate 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: 35.0%

: 1452578-45-8
(3aR,4S,6S,6aR)-methyl 6-(3-bromophenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

: 1452578-49-2
(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 16h; Reflux;
DOI:10.1039/c3ob41082j

Reference yield:

: 108-36-1
1,3-dibromobenzene

: 1452578-49-2
(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 4 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

3.1: chromium(VI) oxide; periodic acid / acetonitrile; water / 3 h / 20 °C

4.1: toluene-4-sulfonic acid / 16 h / Reflux

With chromium(VI) oxide; triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; periodic acid; In tetrahydrofuran; hexane; water; acetonitrile;
DOI:10.1039/c3ob41082j

Reference yield:

: (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

: 1452578-49-2
(2S,3R,4S,5S)-methyl 5-(3-bromophenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 1 h / -40 - 20 °C / Inert atmosphere

2.1: chromium(VI) oxide; periodic acid / acetonitrile; water / 3 h / 20 °C

3.1: toluene-4-sulfonic acid / 16 h / Reflux

With chromium(VI) oxide; triethylsilane; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; periodic acid; In water; acetonitrile;
DOI:10.1039/c3ob41082j