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

Base Information

Chemical Name:((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate
CAS No.:1123172-99-5
Molecular Formula:C₁₇H₂₂F₂N₂O₅S
Molecular Weight:404.435
Hs Code.:

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

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

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

There total 9 articles about ((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate 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: 30.0%

: ((3RS,4SR,5SR)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

: 1123172-99-5
((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

Guidance literature:: With Chiralpak AD-I; In ethanol; n-heptane; optical yield given as %ee; Inert atmosphere;
DOI:10.1021/jm300069y

Reference yield:

: 1123172-89-3
(3,5-difluoro-4-nitrophenyl)methanol

: 1123172-99-5
((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

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

With lithium aluminium tetrahydride; palladium diacetate; phosphorus tribromide; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; n-heptane; tert-butyl methyl ether; acetone;
DOI:10.1021/jm300069y

Reference yield:

: 67567-26-4
4-bromo-2,6-difluoroaniline

: 1123172-99-5
((3R,4S,5S)-5-(3,5-difluoro-4-nitrobenzyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium perborate; acetic acid / 21 h / 65 - 70 °C / Inert atmosphere

2.1: 1-methyl-pyrrolidin-2-one / 6 h / 160 - 165 °C / Inert atmosphere

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

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

4.2: 0.5 h / 25 °C / Cooling with ice; Inert atmosphere

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

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

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

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

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

With 1-methyl-pyrrolidin-2-one; sodium perborate; lithium aluminium tetrahydride; thionyl chloride; palladium diacetate; phosphorus tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; n-heptane; tert-butyl methyl ether; acetone;
DOI:10.1021/jm300069y