4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Base Information

Chemical Name:4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene
CAS No.:866605-84-7
Molecular Formula:C₃₀H₃₀ClNO₉S
Molecular Weight:616.089
Hs Code.:

Synonyms:4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

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Chemical Property of 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

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Technology Process of 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

There total 10 articles about 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene 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: 53.0%

: 842153-79-1
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((5-bromothiophen-2-yl)methyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1692-25-7
3-pyridylboronic acid

: 866605-84-7
4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In 1,2-dimethoxyethane; Inert atmosphere; Reflux;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: C₂₆H₂₈BrClO₁₁S

: 866605-84-7
4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Guidance literature:: Multi-step reaction with 2 steps

1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 0 - 20 °C / Inert atmosphere

2: cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / Inert atmosphere; Reflux

With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; cesium fluoride; In 1,2-dimethoxyethane; water; acetonitrile;
DOI:10.1016/j.bmc.2013.05.048

Reference yield:

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 866605-84-7
4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-[(5-(3-pyridyl)-2-thienyl)methyl]benzene

Guidance literature:: Multi-step reaction with 9 steps

1: mesityllithium / hexane; tetrahydrofuran / 1.5 h / -78 - -63 °C / Inert atmosphere

2: methanesulfonic acid / hexane; tetrahydrofuran / 40.08 h / -78 - 20 °C / Inert atmosphere

3: dmap; N-ethyl-N,N-diisopropylamine / toluene / 1 h / 0 - 20 °C

4: formic acid / 0.5 h / 50 °C

5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C

6: aluminum (III) chloride / dichloromethane / 1.17 h / -78 - 0 °C

7: sodium tetrahydroborate / ethanol; tetrahydrofuran / 2.5 h / 0 °C

8: triethylsilane; boron trifluoride diethyl etherate / acetonitrile; water / 0 - 20 °C / Inert atmosphere

9: cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / Inert atmosphere; Reflux

With triethylsilane; dmap; aluminum (III) chloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; oxalyl dichloride; methanesulfonic acid; boron trifluoride diethyl etherate; mesityllithium; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; cesium fluoride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 1: |Barbier Coupling Reaction;
DOI:10.1016/j.bmc.2013.05.048