Literature DB >> 24476042

Direct synthesis of 2-deoxy-β-glycosides via anomeric O-alkylation with secondary electrophiles.

Danyang Zhu1, Kedar N Baryal, Surya Adhikari, Jianglong Zhu.   

Abstract

An approach for direct synthesis of biologically significant 2-deoxy-β-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-β-tetrasaccharide.

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Year:  2014        PMID: 24476042     DOI: 10.1021/ja4116956

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  19 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Pre-activation Based Stereoselective Glycosylations.

Authors:  Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal:  European J Org Chem       Date:  2017-12-28

3.  Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Authors:  Subbarao Yalamanchili; Dina Lloyd; Clay S Bennett
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

4.  An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

Authors:  Dina Lloyd; Clay S Bennett
Journal:  Chemistry       Date:  2018-05-02       Impact factor: 5.236

5.  Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Padam P Acharya; Jianglong Zhu
Journal:  J Carbohydr Chem       Date:  2019-03-20       Impact factor: 1.667

6.  β-Mannosylation via O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Hai Nguyen; Xiaotian Qi; Cheng Fang; Kevin Saybolt; Xiaohua Li; Peng Liu; Jianglong Zhu
Journal:  European J Org Chem       Date:  2020-03-19

7.  Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide.

Authors:  J Colin Mizia; Clay S Bennett
Journal:  Org Lett       Date:  2019-07-15       Impact factor: 6.005

8.  Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide.

Authors:  Joseph R Romeo; Luca McDermott; Clay S Bennett
Journal:  Org Lett       Date:  2020-04-13       Impact factor: 6.005

Review 9.  A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Authors:  Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2014-07-01       Impact factor: 2.104

10.  Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

Authors:  Jordan T Walk; Zachary A Buchan; John Montgomery
Journal:  Chem Sci       Date:  2015-06-01       Impact factor: 9.825

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