Literature DB >> 32691596

Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.

Wenjing Ye1, Christopher M Stevens1, Peng Wen1, Christopher J Simmons1,2, Weiping Tang1,2.   

Abstract

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.

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Year:  2020        PMID： 32691596      PMCID： PMC8138965          DOI： 10.1021/acs.joc.0c01041

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  33 in total

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Authors:  Steven Fletcher; Michael R Jorgensen; Andrew D Miller
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

4.  Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions.

Authors:  Peng Wen; Christopher J Simmons; Zhi-Xiong Ma; Stephanie A Blaszczyk; Paul G Balzer; Wenjing Ye; Xiyan Duan; Hao-Yuan Wang; Dan Yin; Christopher M Stevens; Weiping Tang
Journal:  Org Lett       Date:  2020-02-06       Impact factor: 6.005

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Journal:  Chem Commun (Camb)       Date:  2016-10-06       Impact factor: 6.222

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Authors:  Myriame Moumé-Pymbock; David Crich
Journal:  J Org Chem       Date:  2012-10-11       Impact factor: 4.354

7.  Microwave-assisted organocatalytic anomerization of alpha-C-glycosylmethyl aldehydes and ketones.

Authors:  Alessandro Massi; Andrea Nuzzi; Alessandro Dondoni
Journal:  J Org Chem       Date:  2007-11-16       Impact factor: 4.354

8.  Intramolecular O-H...O hydrogen-bond-mediated reversal in the partitioning of conformationally restricted triplet 1,4-biradicals and amplification of diastereodifferentiation in their lifetimes.

Authors:  Jarugu Narasimha Moorthy; Subhas Samanta; Apurba L Koner; Satyajit Saha; Werner M Nau
Journal:  J Am Chem Soc       Date:  2008-09-17       Impact factor: 15.419

9.  Nucleofuge Generating Glycosidations by the Remote Activation of Hydroxybenzotriazolyl Glycosides.

Authors:  Mahesh Neralkar; Bijoyananda Mishra; Srinivas Hotha
Journal:  J Org Chem       Date:  2017-11-03       Impact factor: 4.354

10.  Synthetic genistein glycosides inhibiting EGFR phosphorylation enhance the effect of radiation in HCT 116 colon cancer cells.

Authors:  Aleksandra Gruca; Zdzisław Krawczyk; Wiesław Szeja; Grzegorz Grynkiewicz; Aleksandra Rusin
Journal:  Molecules       Date:  2014-11-13       Impact factor: 4.411
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