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Literature DB >> 28584384

Multigram-scale Synthesis of Enantiopure 3,3-Difluoroproline.

Christelle Doebelin¹, Yuanjun He¹, Theodore M Kamenecka¹.

Abstract

An efficient route for the synthesis of enantiopure 3,3-difluoroproline on multigram-scale is described herein. The deoxofluorination can be achieved with DAST on the corresponding racemic pyrrolidinone in good yield. Resolution of the racemate by crystallization with D- and L-tyrosine hydrazide provides both enantiomers of 3,3-difluoroproline in high yield and ee%.

Entities: Chemical Disease Gene

Keywords: 3,3-dilfuoroproline; Chiral resolution; Gram-scale synthesis

Year: 2016 PMID： 28584384 PMCID： PMC5456297 DOI： 10.1016/j.tetlet.2016.11.012

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

15 in total

Review 1. Fluorine in medicinal chemistry.

Authors: Steven Swallow
Journal: Prog Med Chem Date: 2015-01-07

2. Fluorine in a native protein environment--How the spatial demand and polarity of fluoroalkyl groups affect protein folding.

Authors: Christian Jäckel; Mario Salwiczek; Beate Koksch
Journal: Angew Chem Int Ed Engl Date: 2006-06-19 Impact factor: 15.336

Review 3. Applications of Fluorine in Medicinal Chemistry.

Authors: Eric P Gillis; Kyle J Eastman; Matthew D Hill; David J Donnelly; Nicholas A Meanwell
Journal: J Med Chem Date: 2015-07-22 Impact factor: 7.446

4. Solution structure of a small protein containing a fluorinated side chain in the core.

Authors: Gabriel Cornilescu; Erik B Hadley; Matthew G Woll; John L Markley; Samuel H Gellman; Claudia C Cornilescu
Journal: Protein Sci Date: 2006-11-22 Impact factor: 6.725

5. Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.

Authors: Alexandre L'heureux; Francis Beaulieu; Christopher Bennett; David R Bill; Simon Clayton; François Laflamme; Mahmoud Mirmehrabi; Sam Tadayon; David Tovell; Michel Couturier
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

6. Design and Synthesis of Orally Bioavailable 4-Methyl Heteroaryldihydropyrimidine Based Hepatitis B Virus (HBV) Capsid Inhibitors.

Authors: Zongxing Qiu; Xianfeng Lin; Mingwei Zhou; Yongfu Liu; Wei Zhu; Wenming Chen; Weixing Zhang; Lei Guo; Haixia Liu; Guolong Wu; Mengwei Huang; Min Jiang; Zhiheng Xu; Zheng Zhou; Ning Qin; Shuang Ren; Hongxia Qiu; Sheng Zhong; Yuxia Zhang; Yi Zhang; Xiaoyue Wu; Liping Shi; Fang Shen; Yi Mao; Xue Zhou; Wengang Yang; Jim Z Wu; Guang Yang; Alexander V Mayweg; Hong C Shen; Guozhi Tang
Journal: J Med Chem Date: 2016-08-10 Impact factor: 7.446

7. Stereoelectronic effects on collagen stability: the dichotomy of 4-fluoroproline diastereomers.

Authors: Jonathan A Hodges; Ronald T Raines
Journal: J Am Chem Soc Date: 2003-08-06 Impact factor: 15.419

8. Structure-based design of β1i or β5i specific inhibitors of human immunoproteasomes.

Authors: Gerjan de Bruin; Eva M Huber; Bo-Tao Xin; Eva J van Rooden; Karol Al-Ayed; Kyung-Bo Kim; Alexei F Kisselev; Christoph Driessen; Mario van der Stelt; Gijsbert A van der Marel; Michael Groll; Herman S Overkleeft
Journal: J Med Chem Date: 2014-07-15 Impact factor: 7.446

Multigram-scale Synthesis of Enantiopure 3,3-Difluoroproline.

Review 1. Fluorine in medicinal chemistry.

2. Fluorine in a native protein environment--How the spatial demand and polarity of fluoroalkyl groups affect protein folding.

Review 3. Applications of Fluorine in Medicinal Chemistry.

4. Solution structure of a small protein containing a fluorinated side chain in the core.

5. Aminodifluorosulfinium salts: selective fluorination reagents with enhanced thermal stability and ease of handling.

6. Design and Synthesis of Orally Bioavailable 4-Methyl Heteroaryldihydropyrimidine Based Hepatitis B Virus (HBV) Capsid Inhibitors.

7. Stereoelectronic effects on collagen stability: the dichotomy of 4-fluoroproline diastereomers.

8. Structure-based design of β1i or β5i specific inhibitors of human immunoproteasomes.

Review 9. Fluorine in pharmaceuticals: looking beyond intuition.

Review 10. Fluorinated proteins: from design and synthesis to structure and stability.

1. Lipidated cyclopropenes via a stable 3-N spirocyclopropene scaffold.

Review 2. Synthesis of complex unnatural fluorine-containing amino acids.