ChemInform Abstract: The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification.

ChemInform ◽  
2015 ◽  
Vol 46 (19) ◽  
pp. no-no
Author(s):  
Appi Reddy Mandhapati ◽  
Salla Rajender ◽  
Jonathan Shaw ◽  
David Crich
Keyword(s):  
Sialic Acid ◽  
Stereoselective Synthesis ◽  
Protecting Group

The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification

2014 ◽  
Vol 127 (4) ◽  
pp. 1291-1294 ◽  
Author(s):  
Appi Reddy Mandhapati ◽  
Salla Rajender ◽  
Jonathan Shaw ◽  
David Crich
Keyword(s):  
Sialic Acid ◽  
Stereoselective Synthesis ◽  
Protecting Group

Amide Bond Formation of Sialic Acid in Oligosaccharide without Protecting Group

Heterocycles ◽  
2018 ◽  
Vol 97 (2) ◽  
pp. 1203 ◽  
Author(s):  
Shino Manabe ◽  
Junpei Abe ◽  
Yukishige Ito
Keyword(s):  
Sialic Acid ◽  
Bond Formation ◽  
Amide Bond ◽  
Protecting Group ◽  
Amide Bond Formation

Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group

2020 ◽  
Vol 85 (24) ◽  
pp. 16166-16181
Author(s):  
Nahoko Yagami ◽  
Amol M. Vibhute ◽  
Hide-Nori Tanaka ◽  
Naoko Komura ◽  
Akihiro Imamura ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Protecting Group ◽  
Glycosyl Donors

scholarly journals SnCl4-catalyzed Solvent-free Acetolysis of 2,7-Anhydrosialic Acid Derivatives

2019 ◽  
Author(s):  
Kesatebrhan Haile Asressu ◽  
Cheng-Chung Wang
Keyword(s):  
Sialic Acid ◽  
Lewis Acids ◽  
Ring Opening ◽  
Building Blocks ◽  
Solvent Free ◽  
Biologically Active ◽  
Protecting Group ◽  
Free Ring ◽  
Ring Opening Reactions ◽  
Acid Catalyzed

Sialic acid-containing glycans are found in different sialic acid forms and a variety of glycosidic linkages in biologically active glycoconjugates. Hence, the preparation of suitably protected sialyl building blocks requires high attention in order to access glycans in pure form. In this line, various C-5 substituted 2,7-anhydrosialic acid derivatives bearing both electron donating and withdrawing protecting groups were synthesized and subjected to different Lewis acid-catalyzed solvent free ring opening reactions at room temperature in the presence of acetic anhydride. Among the various Lewis acids tested, the desired acetolysized products were obtained in moderate yields under a tin(IV) chloride catalysis system. Our methodology can be extended to regioselective protecting group installation and manipulation towards a number of thiosialoside and halide donors.

scholarly journals An Efficient Synthesis of Tetrodotoxin

2021 ◽  
Author(s):  
David Konrad ◽  
Peter Ruehmann ◽  
Hiroyasu Ando ◽  
Belinda Hetzler ◽  
Bryan Matsuura ◽  
...  
Keyword(s):  
Tertiary Amine ◽  
Stereoselective Synthesis ◽  
Primary Alcohol ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Protecting Group ◽  
Efficient Synthesis ◽  
Ready Access ◽  
Biologically Active Derivatives ◽  
Glucose Derivative

Tetrodotoxin (TTX) is an indispensable probe in neuroscience, a biosynthetic and ecological enigma, and one of the most celebrated targets of synthetic chemistry. Here, we present a stereoselective synthesis of TTX that proceeds in 22 steps starting from a readily available glucose derivative. The central cyclohexane ring of TTX and its α-tertiary amine moiety was established via the intramolecular 1,3-dipolar cycloaddition of a nitrile oxide, followed by alkynyl addition to the resultant isoxazoline. After some carefully chosen protecting group manipulations, a ruthenium-catalyzed hydroxylactonization set the stage for the formation of its dioxa-adamantane core. Installation of the guanidine, oxidation of a primary alcohol, and late-stage epimerization of the resultant aldehyde gave a mixture of TTX and anhydro TTX. Our synthesis represents one of the most effective of TTX reported to date and could give ready access to biologically active derivatives.

Protecting Group Strategies for Sialic Acid Derivatives

2018 ◽  
pp. 283-306
Author(s):  
Harsha Amarasekara ◽  
Szymon Buda ◽  
Appi R. Mandhapati ◽  
David Crich
Keyword(s):  
Sialic Acid ◽  
Protecting Group
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