Unusual addition of amines to C-2 of vinyl sulfone-modified-beta-D-pent-2-enofuranosyl carbohydrates: synthesis of a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides.
When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-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 beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides.
Das
Indrajit
I
Department of Chemistry, Indian Institute of Technology, Kharagpur, India.
Suresh
Cheravakkattu G
CG
Décout
Jean-Luc
JL
Pathak
Tanmaya
T
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D000617:Aminoglycosides / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D000588:Amines; D000606:Amino Sugars; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D003837:Deoxy Sugars; D005663:Furans; D013450:Sulfones; C009873:divinyl sulfone