(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

Base Information

Chemical Name:(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol
CAS No.:1359717-98-8
Molecular Formula:C₁₅H₁₆F₂O₃
Molecular Weight:282.287
Hs Code.:

Synonyms:(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-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 (4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

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Technology Process of (4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

There total 7 articles about (4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-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: 31.0%

: 1359717-96-6
(2R,3S,4R)-2-acetoxy-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-hex-5-yne

: 1359717-98-8
(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tert-butyl alcohol; at 80 ℃; for 1.75h; Inert atmosphere;
DOI:10.1016/j.jfluchem.2011.02.015

Reference yield:

: 171622-74-5
(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

: 1359717-98-8
(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Dess-Martin periodane

2.1: potassium carbonate / methanol / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 1 h / -60 °C / Molecular sieve; Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

6.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tert-butyl alcohol / 1.75 h / 80 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium carbonate; Dess-Martin periodane; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Dess-Martin oxidation;
DOI:10.1016/j.jfluchem.2011.02.015

Reference yield:

: 171863-59-5
(((2R,3R)-2,3-bis(benzyloxy)pent-4-yn-1-yl)oxy)(tert-butyl)dimethylsilane

: 1359717-98-8
(4S,5R)-5-(O-acetyl)-4-(O-benzyl)-1,1-difluoro-2-methylcyclopent-2-en-4,5-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: tetrabutylammonium triphenyldifluorosilicate / N,N-dimethyl-formamide / 1 h / -60 °C / Molecular sieve; Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tert-butyl alcohol / 1.75 h / 80 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Dess-Martin oxidation;
DOI:10.1016/j.jfluchem.2011.02.015