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Critical Influence of 5‐Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
Author(s) -
Galkin Konstantin I.,
Krivodaeva Elena A.,
Romashov Leonid V.,
Zalesskiy Sergey S.,
Kachala Vadim V.,
Burykina Julia V.,
Ananikov Valentine P.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602883
Subject(s) - yield (engineering) , decomposition , biomass (ecology) , 5 hydroxymethylfurfural , chemistry , molecule , chemical process of decomposition , derivative (finance) , organic chemistry , hydrogen bond , hydroxymethylfurfural , chemical engineering , materials science , catalysis , oceanography , furfural , economics , financial economics , engineering , metallurgy , geology
Abstract Spectral studies revealed the presence of a specific arrangement of 5‐hydroxymethylfurfural (5‐HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5‐HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac®) was synthesized with only 15 % yield starting from 5‐HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5‐HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5‐HMF decomposition in solution were established by NMR and ESI‐MS studies. A highly selective synthesis of a 5‐HMF derivative from glucose was achieved using a protecting group at O(6) position.