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Literature DB >> 25470411

C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation.

Jyh-Herng Ruei¹, Patteti Venukumar, Arun B Ingle, Kwok-Kong Tony Mong.

Abstract

We reported a remote control glycosylation method using the picoloyl protecting group for 2-deoxy-β-glycosidic bond formation. The method is applicable to various 2-deoxythioglycosyl donors and the utility is illustrated by the synthesis of a deoxytrisaccharide component of landomycins.

Entities: Chemical

Mesh：

Substances：
Glycosides

Year: 2015 PMID： 25470411 DOI： 10.1039/c4cc08465a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

11 in total

Review 1. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors: Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

2. Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal.

Authors: Scott A Geringer; Michael P Mannino; Mithila D Bandara; Alexei V Demchenko
Journal: Org Biomol Chem Date: 2020-07-01 Impact factor: 3.876

Review 3. Oligosaccharide Synthesis and Translational Innovation.

Authors: Larissa Krasnova; Chi-Huey Wong
Journal: J Am Chem Soc Date: 2019-02-18 Impact factor: 15.419

4. 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

5. 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

6. 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

7. 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