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Chirale Lactole, XII. Untersuchungen zur basenkatalysierten Glycolaldehydaldolisierung
Author(s) -
Noe Christian R.,
Knollmüller Max,
Ettmayer Peter,
Freissmuth Jerome
Publication year - 1994
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.199419940611
Subject(s) - glycolaldehyde , chemistry , hexose , galactose , derivative (finance) , catalysis , sugar , anomer , organic chemistry , stereochemistry , financial economics , economics , enzyme
Chiral Lactols, XII. – Studies on the Aldolization of Glycolaldehyde Catalyzed by Bases Base‐catalyzed aldolization of the glycolaldehyde derivative 1 is studied under various reaction conditions. The resulting products, tetrose and hexose derivatives 2–11 , are reduced to the corresponding sugar alcohols and analyzed by HPL chromatography. All experiments leading to a trimerization of 1 give threose 3 as major product among the tetroses and allose 4 among the hexoses. An exception is the reaction catalyzed by LiOH, in which trimerization of 1 to the corresponding hexose derivatives proceeds much slower and as products galactose 10 together with glucose 6 are favored above the other hexoses.