Synthetic Route of 14215-68-0. Let¡¯s face it, organic chemistry can seem difficult to learn. Especially from a beginner¡¯s point of view. Like 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide. In a document type is Article, introducing its new discovery.
One-pot stereoselective synthesis of beta-N-aryl-glycosides by N-glycosylation of aromatic amines: application to the synthesis of tumor-associated carbohydrate antigen building blocks
We studied the stereoselective synthesis of several beta-N-aryl-glycosides by glycosylation of aromatic primary amines using unprotected carbohydrates in aqueous solution. This was the first report showing an efficient method for the synthesis with one step of beta-N-glycosyl-para-amino-phenyl alanine building blocks for the tumor-associated carbohydrate antigen (TACA) glycopeptides synthesis. Analysis of products by 1H and 13C NMR indicated that the Amadori rearrangement had not occurred after formation of the stereoselective beta-N-glycoside bond (natural N-glycoprotein linkage). The study of the chemical and enzymatic stability in aqueous media of beta-N-aryl-glycosides synthesized was also investigated. For the first time we have shown that the N-glycosidic bond was relatively stable at pH near to 7 and more stable than the O-glycosidic bond to enzymatic hydrolysis. This higher enzymatic and chemical stability of the N-glycosidic bond is essential to envisage further development of stable TACA building blocks.
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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics