(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

Base Information

Chemical Name:(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide
CAS No.:1452578-77-6
Molecular Formula:C₂₁H₁₇NO₅
Molecular Weight:363.37
Hs Code.:

Synonyms:(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

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Chemical Property of (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

Chemical Property:

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Technology Process of (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

There total 3 articles about (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-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: 38.0%

: 1452578-76-5
(2S,3R,4S,5S)-methyl 3,4-dihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxylate

: 1452578-77-6
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

Guidance literature:: With hydroxylamine hydrochloride; sodium methylate; In methanol; at 20 ℃; for 16h;
DOI:10.1039/c3ob41082j

Reference yield:

: 1452578-73-2
(3aR,4S,6S,6aR)-methyl 2,2-dimethyl-6-(4-((trimethylsilyl)ethynyl)phenyl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

: 1452578-77-6
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1: silver nitrate; water / acetone / 24 h / 20 °C / Darkness

2: copper(l) chloride; N-butylamine; hydroxylamine hydrochloride / water / 0 °C

3: toluene-4-sulfonic acid / methanol / 48 h / Reflux

4: hydroxylamine hydrochloride; sodium methylate / methanol / 16 h / 20 °C

With hydroxylamine hydrochloride; water; sodium methylate; toluene-4-sulfonic acid; silver nitrate; N-butylamine; copper(l) chloride; In methanol; water; acetone; 2: |Cadiot-Chodkiewicz Coupling;
DOI:10.1039/c3ob41082j

Reference yield:

: 1452578-74-3
(3aR,4S,6S,6aR)-methyl 6-(4-ethynylphenyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

: 1452578-77-6
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(phenylbuta-1,3-diyn-1-yl)phenyl)tetrahydrofuran-2-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: copper(l) chloride; N-butylamine; hydroxylamine hydrochloride / water / 0 °C

2: toluene-4-sulfonic acid / methanol / 48 h / Reflux

3: hydroxylamine hydrochloride; sodium methylate / methanol / 16 h / 20 °C

With hydroxylamine hydrochloride; sodium methylate; toluene-4-sulfonic acid; N-butylamine; copper(l) chloride; In methanol; water; 1: |Cadiot-Chodkiewicz Coupling;
DOI:10.1039/c3ob41082j