1038619-76-9Relevant academic research and scientific papers
Unusual addition of amines to C-2 of vinyl sulfone-modified-β-d-pent-2-enofuranosyl carbohydrates: synthesis of a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides
Das, Indrajit,Suresh, Cheravakkattu G.,Decout, Jean-Luc,Pathak, Tanmaya
, p. 1287 - 1296 (2008/09/21)
When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the β-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the 'unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the d-arabino configuration. Selected products were desulfonylated to obtain a new class of β-anomeric 2-amino-2,3-dideoxy-d-threo-pentofuranosides.
