(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

Base Information

Chemical Name:(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
CAS No.:1452578-71-0
Molecular Formula:C₁₇H₂₁NO₅
Molecular Weight:319.357
Hs Code.:

Synonyms:(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

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Chemical Property of (2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

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Technology Process of (2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

There total 4 articles about (2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide 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: 18.0%

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

: 1452578-71-0
(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

Guidance literature:: With hydroxylamine hydrochloride; sodium methylate; In methanol; at 20 ℃; for 48h;
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

: 1452578-71-0
(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

Guidance literature:: Multi-step reaction with 4 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

4: hydroxylamine hydrochloride; sodium methylate / methanol / 48 h / 20 °C

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

Reference yield:

: C₁₄H₁₅IO₅

: 1452578-71-0
(2S,3R,4S,5S)-5-(4-(hex-1-yn-1-yl)phenyl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide

Guidance literature:: Multi-step reaction with 3 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

3: hydroxylamine hydrochloride; sodium methylate / methanol / 48 h / 20 °C

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