Addition of amines and carbon nucleophiles to vinyl sulfone-modified 6-deoxy-hex-3-enopyranoside: a case of nucleophile dependent diastereoselectivity

作者：Bhattacharya Raw; Pathak Tanmaya^*

来源：Carbohydrate Research, 2009, 344(17): 2336-2341.

DOI：10.1016/j.carres.2009.09.009

• Vinyl sulfone
• Modified carbohydrate
• Michael addition
• Aminosugar
• Branched-chain sugar
• 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).

• 出版日期2009-11-23