(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

Base Information

Chemical Name:(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol
CAS No.:1417339-38-8
Molecular Formula:C₇H₁₂F₃NO₂
Molecular Weight:199.173
Hs Code.:

Synonyms:(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

Chemical Property:

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Technology Process of (1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

There total 13 articles about (1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol 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: 65.0%

: 1417339-37-7
(3aS,4S,5R,6S,7aS)-3-acetyl-5-((tert-butyldimethylsilyl)oxy)-6-(difluoromethyl)-4-fluorohexahydrobenzo[d]oxazol-2(3H)-one

: 1417339-38-8
(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

Guidance literature:: With water; lithium hydroxide; In methanol; water; for 20h; Reflux;

Reference yield:

: 1349172-44-6
(3aS,4R,5R,6R,7aS)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-hexahydrobenzo[d]oxazol-2(3H)-one

: 1417339-38-8
(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1: boron trichloride / dichloromethane / 4 h

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3.5 h / 60 °C

3: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 20 h / 20 °C / Inert atmosphere

4: acetic acid / 4 h / 60 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C

6: acetic acid / methanol / 16 h / 60 °C

7: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

8: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

9: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; tetrahydrofuran / 17 h / 0 - 20 °C / Inert atmosphere

10: water; lithium hydroxide / water; methanol / 20 h / Reflux

With 1H-imidazole; water; boron trichloride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 130970-85-3
rac-((((1R,2R,6R)-6-((benzyloxy)methyl)cyclohex-3-ene-1,2-diyl)bis-(oxy))bis(methylene))dibenzene

: 1417339-38-8
(1S,2S,3S,4R,5S)-2-amino-5-(difluoromethyl)-3-fluorocyclohexane-1,4-diol

Guidance literature:: Multi-step reaction with 14 steps

1: water; N-Bromosuccinimide / dimethyl sulfoxide; water / 2.5 h / 0 - 20 °C

2: dichloromethane / 1.5 h / 0 - 20 °C

3: sodium hydride / tetrahydrofuran; mineral oil / 21.5 h / 0 °C / Reflux

4: Chiralpak IA / hexane; ethanol / Resolution of racemate

5: boron trichloride / dichloromethane / 4 h

6: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3.5 h / 60 °C

7: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 20 h / 20 °C / Inert atmosphere

8: acetic acid / 4 h / 60 °C

9: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C

10: acetic acid / methanol / 16 h / 60 °C

11: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

12: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

13: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane; tetrahydrofuran / 17 h / 0 - 20 °C / Inert atmosphere

14: water; lithium hydroxide / water; methanol / 20 h / Reflux

With 1H-imidazole; N-Bromosuccinimide; water; boron trichloride; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;