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Novel 1,6‐Stannylenes of Glucose, Galactose and Mannose
Author(s) -
Köpper Sabine,
Brandenburg Anna
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201154
Subject(s) - chemistry , dimer , tin , mannose , derivative (finance) , galactose , monomer , atom (system on chip) , stereochemistry , medicinal chemistry , combinatorial chemistry , polymer chemistry , organic chemistry , polymer , computer science , financial economics , economics , embedded system
Treatment of 2,3,4‐tri‐ O ‐benzyl‐gluco‐, manno‐ and ‐galactopyranose with dibutyltin oxide leads to the 1,6‐di‐ O ‐stannylene products 2, 5 and 7 , whereas no such products are formed by treatment of the 3‐ O ‐axially configured ido and allo sugars. Spectroscopic studies show that the tin atom is hexacoordinated in these compounds. The gluco derivative mainly exists as a dimer while the manno and galacto compounds are monomeric. All stannylenes easily eliminate the 3‐ O ‐benzyl group and are stereospecifically opened to give 6‐substituted α,β‐unsaturated aldehydes 3, 8 and 9 . Both formation and further reactions can be correlated with the tendency of the tin atom to extend its coordination.