Addition of amines and carbon nucleophiles to vinyl sulfone-modified 6-deoxy-hex-3-enopyranoside: a case of nucleophile dependent diastereoselectivity.
Reactions of amines and carbon nucleophiles with 4-sulfonyl-hex-3-enopyranoside generate a range of C-3 amino- and C-3 branched-chain sugars, which are analogues of 3-amino-3,6-dideoxy sugars and 3-C-branched-chain-3,6-dideoxy sugars. The diastereoselectivity of addition reaction is nucleophile dependent; while both nitrogen and carbon nucleophiles added in cis-fashion, amines generated C3-C4 trans-diaxial products (gulo-derivatives), and carbon nucleophiles afforded C3-C4 trans-diequatorial products (gluco-analogues).
Bhattacharya
Rahul
R
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721 302, India.
Pathak
Tanmaya
T
D000588:Amines / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D000588:Amines; D000606:Amino Sugars; D003837:Deoxy Sugars; D013450:Sulfones; C009873:divinyl sulfone