title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, India.
authors.forename: Indrajit
authors.initials: I
authors.lastname: Das
authors.forename: Cheravakkattu G
authors.initials: CG
authors.lastname: Suresh
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Décout
authors.forename: Tanmaya
authors.initials: T
authors.lastname: Pathak
mesh_terms: 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*
chemical_list: D000588:Amines; D000606:Amino Sugars; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D003837:Deoxy Sugars; D005663:Furans; D013450:Sulfones; C009873:divinyl sulfone