(3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride

Base Information

• Chemical Name: (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride
• CAS No.: 1204343-92-9
• Molecular Formula: C₁₅H₁₅F₇N₂O₆S*ClH
• Molecular Weight: 520.81
• Mol file: 1204343-92-9.mol

Synonyms:(3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride

Chemical Property of (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride

There total 11 articles about (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride 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:

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 (1204343-91-8) → (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride (1204343-92-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; 1,4-dioxane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm300069y

Reference yield:

3,5-difluoro-4-nitro-benzonitrile (1123172-88-2) → (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride (1204343-92-9)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; lithium aluminium tetrahydride; thionyl chloride; potassium peroxymonosulfate; palladium diacetate; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; n-heptane; tert-butyl methyl ether; water; acetone;

DOI:10.1021/jm300069y

Reference yield:

C21H24F2N2O7S → (3R,4S,5S)-3-amino-5-(3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)-4-nitrobenzyl)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide hydrochloride (1204343-92-9)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

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

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

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

With hydrogenchloride; lithium aluminium tetrahydride; potassium peroxymonosulfate; palladium diacetate; potassium hexamethylsilazane; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; n-heptane; tert-butyl methyl ether; water;

DOI:10.1021/jm300069y

upstream raw materials:

3,5-difluoro-4-nitro-benzonitrile

methyl 3,5-difluoro-4-nitrobenzoate

(3,5-difluoro-4-nitrophenyl)methanol

((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

Downstream raw materials:

(3S,4S,5R)-3-(4-amino-3-fluoro-5-((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)benzyl)-5-(((4-(tertbutyl)pyridin-2-yl)methyl)amino)-4-hydroxytetrahydro-2H-thiopyran 1,1-dioxide

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

(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

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

Refernces