(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Base Information

Chemical Name:(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate
CAS No.:1452578-69-6
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

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Chemical Property of (2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

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Technology Process of (2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

There total 3 articles about (2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-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: 92.0%

: 1395409-48-9
methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-iodophenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

: 693-02-7
hex-1-yne

: 1452578-69-6
(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In acetonitrile; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1039/c3ob41082j

Reference yield:

: 1395409-44-5
(R)-1-[(3aS,4R,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethane-1,2-diol

: 1452578-69-6
(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: chromium(VI) oxide; periodic acid / acetonitrile; water / 20 °C

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

3: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 2 h / 20 °C / Inert atmosphere

With chromium(VI) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; toluene-4-sulfonic acid; periodic acid; triethylamine; In water; acetonitrile; 3: |Sonogashira Cross-Coupling;
DOI:10.1039/c3ob41082j

Reference yield:

: C₁₄H₁₅IO₅

: 1452578-69-6
(2S,3R,4S,5S)-methyl 5-(4-(hex-1-yn-1-yl)phenyl)-3,4-dihydroxytetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 2 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; toluene-4-sulfonic acid; triethylamine; In acetonitrile; 2: |Sonogashira Cross-Coupling;
DOI:10.1039/c3ob41082j