methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

Base Information

Chemical Name:methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate
CAS No.:1395409-50-3
Molecular Formula:C₂₅H₂₇NO₆
Molecular Weight:437.492
Hs Code.:

Synonyms:methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

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Chemical Property of methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

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Technology Process of methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

There total 9 articles about methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-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: 26.0%

: 933986-59-5
4-(morpholinomethyl)phenylacetylene

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

: 1395409-50-3
methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

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

Reference yield:

: C₁₈H₂₃IO₅

: 1395409-50-3
methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / methanol / 20 °C

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

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

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

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

Reference yield:

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

: 1395409-50-3
methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: -40 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol / 20 °C

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

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

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

With chromium(VI) oxide; triethylsilane; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; periodic acid; triethylamine; In methanol; water; acetonitrile; 5.1: |Sonogashira Cross-Coupling;
DOI:10.1039/c3ob41082j