(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
CAS No.:1313513-49-3
Molecular Formula:C₂₁H₂₂ClNO₇S
Molecular Weight:467.927
Hs Code.:

Synonyms:(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

There total 16 articles about (2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol 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: 20.0%

: 1313513-48-2
2-(4-(allyloxymethyl)-2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-5-(furan-2-yl)thiazole

: 1313513-49-3
(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

: 1313513-53-9
(2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: 2-(4-(allyloxymethyl)-2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-5-(furan-2-yl)thiazole; With boron trichloride; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With methanol; In dichloromethane;
DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

: 1313513-45-9
C₁₇H₂₆BrClO₃Si

: 1313513-49-3
(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

: 1313513-53-9
(2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 9 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 75 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

3.3: -50 - -10 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: pyridine; phosphorus tribromide / diethyl ether / 0 - 20 °C / Inert atmosphere; Reflux

5.2: 1 h / 85 °C / Inert atmosphere

6.1: sodium hydroxide / ethanol; water / 15 h / 100 °C / Inert atmosphere

6.2: 0 °C

7.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

8.1: Lawessons reagent / tetrahydrofuran / Inert atmosphere; Reflux

9.1: boron trichloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

With Lawessons reagent; 4-methyl-morpholine; pyridine; n-butyllithium; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; boron trichloride; phosphorus tribromide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

: 1313513-42-6
methyl 4-(acetoxymethyl)-2-bromo-5-chlorobenzoate

: 1313513-49-3
(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

: 1313513-53-9
(2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 15 h / 20 °C / Inert atmosphere

1.2: 0 °C

2.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

3.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 75 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

5.2: -78 °C / Inert atmosphere

5.3: -50 - -10 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

7.1: pyridine; phosphorus tribromide / diethyl ether / 0 - 20 °C / Inert atmosphere; Reflux

7.2: 1 h / 85 °C / Inert atmosphere

8.1: sodium hydroxide / ethanol; water / 15 h / 100 °C / Inert atmosphere

8.2: 0 °C

9.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

10.1: Lawessons reagent / tetrahydrofuran / Inert atmosphere; Reflux

11.1: boron trichloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

With Lawessons reagent; 4-methyl-morpholine; pyridine; 1H-imidazole; dmap; n-butyllithium; lithium hydroxide monohydrate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; boron trichloride; phosphorus tribromide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.ejmech.2011.03.052