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Chemical Synthesis of 1‐Deoxy‐ L ‐fructose and L ‐Sorbose Through Carbonyl Translocation
Author(s) -
Wu HsinPei,
Hsu NaiYun,
Lu TaiNi,
Chang CheChien
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403196
Subject(s) - chemistry , yield (engineering) , sorbose , fructose , total synthesis , alcohol , derivative (finance) , chemical synthesis , diol , organic chemistry , stereochemistry , biochemistry , in vitro , materials science , economics , financial economics , metallurgy
Two rare sugars – 1‐deoxy‐ L ‐fructose and L ‐sorbose – were synthesized from inexpensive starting materials by a carbonyl translocation method developed in our laboratory. Reduction of a known starting compound gave a 1,5‐diol derivative. Selective protection of the corresponding primary alcohol and oxidation of the secondary alcohol provided the desired product in acyclic, protected form. Subsequent deprotection resulted in the production of 1‐deoxy‐ L ‐fructose from the known starting material in five steps and in a total yield of 42 %. This approach represents the first report of a chemical synthesis of 1‐deoxy‐ L ‐fructose. A similar strategy was applied to convert inexpensive D ‐glucose into L ‐sorbose, which was prepared in five steps from a known starting material in a total yield of 55 %. The synthetic methods represent a complementary method to biological approaches for the synthesis of vitamin C.