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.

Cite: Galkin K.I. , Krivodaeva E.A. , Romashov L.V. , Zalesskiy S.S. , Kachala V.V. , Burykina J.V. , Ananikov V.P.
Critical Influence of 5‐Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
Angewandte Chemie International Edition. 2016. V.55. N29. P.8338-8342. DOI: 10.1002/anie.201602883 WOS Scopus OpenAlex

Identifiers:

≡ Web of science:	WOS:000383253300026
≡ Scopus:	2-s2.0-84973575848
≡ OpenAlex:	W2412664088

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