Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides

2014 ◽  
Vol 12 (40) ◽  
pp. 7900-7903 ◽  
Author(s):  
Madhu Babu Tatina ◽  
Anil Kumar Kusunuru ◽  
Syed Khalid Yousuf ◽  
Debaraj Mukherjee
Keyword(s):  
Stereoselective Synthesis ◽  
Zinc Dust ◽  
Terminal Alkynes ◽  
Ethyl Bromoacetate ◽  
Glycosyl Donors

Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated aromatic and aliphatic acetylenes. Different glycosyl donors such as glycals and anomeric acetates were tested towards in situ generated alkynyl zinc reagent using zinc dust and ethyl bromoacetate. The method provides a simple, mild and stereoselective access of alkynyl glycosides.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

scholarly journals Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters

2015 ◽  
Vol 51 (43) ◽  
pp. 8939-8941 ◽  
Author(s):  
Sandra Medina ◽  
Alexander S. Henderson ◽  
John F. Bower ◽  
M. Carmen Galan
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Co Catalysts ◽  
New Class ◽  
Stereoselective Glycosylation ◽  
Glycosyl Donors

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described.

scholarly journals Alkoxide-catalyzed addition of alkyl carbonates across alkynes – stereoselective synthesis of (E)-β-alkoxyacrylates

2017 ◽  
Vol 19 (3) ◽  
pp. 643-646
Author(s):  
Timo Wendling ◽  
Eugen Risto ◽  
Benjamin Erb ◽  
Lukas J. Gooßen
Keyword(s):  
Stereoselective Synthesis ◽  
Terminal Alkynes ◽  
Potassium Methoxide ◽  
Stereoselective Addition

Terminal alkynes were converted to (E)-β-alkoxyacrylates via regio- and stereoselective addition of dialky carbonates catalyzed by potassium methoxide.

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

Supramolecular Control of Photocycloadditions in Solution: In Situ Stereoselective Synthesis and Release of Cyclobutanes

2019 ◽  
Vol 131 (12) ◽  
pp. 4026-4031 ◽  
Author(s):  
Li‐Li Ma ◽  
Yuan‐Yuan An ◽  
Li‐Ying Sun ◽  
Yao‐Yu Wang ◽  
F. Ekkehardt Hahn ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Supramolecular Control

scholarly journals Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization

2020 ◽  
Vol 11 (23) ◽  
pp. 5944-5949 ◽  
Author(s):  
Guo-Ming Ho ◽  
Lucas Segura ◽  
Ilan Marek
Keyword(s):  
Stereoselective Synthesis ◽  
In Situ Functionalization

A regio- and stereoselective ruthenium-catalyzed isomerization of ω-alkenyl boronates into stereodefined di- and trisubstituted alkenylboronate derivatives is reported.

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