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Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

ABSTRACT: L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.

SUBMITTER: Foster RW

PROVIDER: S-EPMC4648048 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

Foster Robert W RW Tame Christopher J CJ Bučar Dejan-Krešimir DK Hailes Helen C HC Sheppard Tom D TD

Chemistry (Weinheim an der Bergstrasse, Germany) 20150925 45

L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well ...[more]

PMID: 26407081

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Project description:We report on the synthesis and characterization of novel mesoporous chiral polyboronates obtained by condensation of (R,S)/(S,S)-hexane-1,2,5,6-tetrol (HT) with simple aromatic diboronic acids (e.g., 1,3-benzenediboronic acid) (BDB). HT is a cellulose-derived building block comprising two 1,2-diol structures linked by a flexible ethane bridge. It typically consists of two diastereomers one of which [(S,R)-HT] can be made chirally pure. Boronic acids are abundantly available due to their importance in Suzuki-Miyaura coupling reactions. They are generally considered nontoxic and easy to synthesize. Reactive dissolution of generally sparingly soluble HT with BDB, in only a small amount of solvent, yields the mesoporous HT/polyboronate materials by spontaneous precipitation from the reaction mixture. The 3D nature of HT/polyboronate materials results from the entanglement of individual 1D polymeric chains. The obtained BET surface areas (SAs) and pore volumes (PVs) depend strongly on HT's diastereomeric excess and the meta/para orientation of the boronic acids on the phenyl ring. This suggests a strong influence of the curvature(s) of the 1D polymeric chains on the final materials' properties. Maximum SA and PV values are respectively 90 m2 g-1 and 0.44 mL g-1. Variably sized mesopores, spanning mainly the 5-50 nm range, are evidenced. The obtained pore volumes rival the ones of some covalent organic frameworks (COFs), yet they are obtained in a less expensive and more benign fashion. Moreover, currently no COFs have been reported with pore diameters in excess of 5 nm. In addition, chiral boron-based COFs have presently not been reported. Scanning electron microscopy reveals the presence of micrometer-sized particles, consisting of aggregates of plates, forming channels and cell-like structures. X-ray diffraction shows the crystalline nature of the material, which depends on the nature of the aromatic diboronic acids and, in the specific case of 1,4-benzenediboronic acid, also on the applied diastereomeric excess in HT.

Dataset Information

Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

Publications

Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.

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