(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

Base Information

Chemical Name:(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide
CAS No.:1367877-91-5
Molecular Formula:C₂₄H₃₀F₇N₃O₅S
Molecular Weight:605.574
Hs Code.:

(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

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Chemical Property of (3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

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Technology Process of (3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

There total 14 articles about (3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide 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:

: 1123172-45-1
5-(2,2-dimethyl-propyl)-isoxazole-3-carbaldehyde

: 1367877-85-7
(3R,4S,5S)-3-amino-5-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide

: 1367877-91-5
(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

Guidance literature:: 5-(2,2-dimethyl-propyl)-isoxazole-3-carbaldehyde; (3R,4S,5S)-3-amino-5-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide; With sodium acetate; In methanol; dichloromethane; at 25 ℃; for 17h; Inert atmosphere;

With sodium cyanoborohydride; In methanol; dichloromethane; for 1h; Inert atmosphere;
DOI:10.1021/jm300069y

Reference yield:

: 1204343-91-8
tert-butyl ((3R,4S,5S)-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2Hthiopyran-3-yl)carbamate

: 1367877-91-5
(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 2 h / 25 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; ammonia; hydrogen / methanol / 50 h / 25 °C / Inert atmosphere

3.1: sodium acetate / methanol; dichloromethane / 17 h / 25 °C / Inert atmosphere

3.2: 1 h / Inert atmosphere

With hydrogenchloride; palladium 10% on activated carbon; ammonia; hydrogen; sodium acetate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jm300069y

Reference yield:

: 1123172-88-2
3,5-difluoro-4-nitro-benzonitrile

: 1367877-91-5
(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-4-hydroxy-5-(((5-neopentylisoxazol-3-yl)methyl)amino)tetrahydro-2H-thiopyran 1,1-dioxide

Guidance literature:: Multi-step reaction with 12 steps

1.1: thionyl chloride / 0 - 25 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / 0 - 5 °C / Inert atmosphere

2.2: 0.5 h / 25 °C / Cooling with ice; Inert atmosphere

3.1: phosphorus tribromide / 24 h / 25 °C / Inert atmosphere

4.1: potassium carbonate / acetone / 2.5 h / 25 - 30 °C / Inert atmosphere

5.1: palladium diacetate; triethylamine; triphenylphosphine / tert-butyl methyl ether / 16 h / 25 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / -70 °C / Inert atmosphere

7.1: Chiralpak AD-I / ethanol; n-heptane / Inert atmosphere

8.1: potassium hexamethylsilazane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere

9.1: potassium peroxymonosulfate / tetrahydrofuran; water / 2 h / 25 °C / Inert atmosphere

10.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 2 h / 25 °C / Inert atmosphere

11.1: palladium 10% on activated carbon; ammonia; hydrogen / methanol / 50 h / 25 °C / Inert atmosphere

12.1: sodium acetate / methanol; dichloromethane / 17 h / 25 °C / Inert atmosphere

12.2: 1 h / Inert atmosphere

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; potassium peroxymonosulfate; palladium 10% on activated carbon; ammonia; hydrogen; sodium acetate; palladium diacetate; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; n-heptane; dichloromethane; tert-butyl methyl ether; water; acetone;
DOI:10.1021/jm300069y