Dianhydrohexitols

Dianhydrohexitols are heterocyclic compounds with the formula [OCH₂CH(OH)CH]₂. These diols are colorless solids that are derived from sugars, and thus are of interest as renewable feedstocks.

The three isomers are obtained by double dehydration of hexitols such as mannitol and sorbitol. The hexitols themselves are obtained by hydrogenation of abundant sugars mannose and glucose. Among these diols the 1,4- and 3,6-dianhydrohexitols are well known under the names isosorbide, isoidide, and isomannide.[1][2][3]

1,4:3,6-dianhydrohexitols


Isosorbide	Isoidide	Isomannide
1,4:3,6-dianhydro-D-glucidol	1,4:3,6-dianhydro-L-iditol	1,4:3,6-dianhydro-D-mannitol

References

Cope, Arthur C.; Shen, T. Y. (1956). "The Stereochemistry of 1,4: 3,6-Dianhydrohexitol Derivatives1". Journal of the American Chemical Society. 78 (13): 3177. doi:10.1021/ja01594a055.
Le Nôtre, Jérôme; Van Haveren, Jacco; Van Es, Daan S. (2013). "Synthesis of Isoidide through Epimerization of Isosorbide using Ruthenium on Carbon". ChemSusChem. 6 (4): 693–700. doi:10.1002/cssc.201200714. PMID 23457114.
Wu, Jing; Thiyagarajan, Shanmugam; Fonseca Guerra, Célia; Eduard, Pieter; Lutz, Martin; Noordover, Bart A. J.; Koning, Cor E.; Van Es, Daan S. (2017). "Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals". ChemSusChem. 10 (16): 3202–3211. doi:10.1002/cssc.201700617. hdl:1871.1/e9774e3a-858a-4003-97a6-4640b04b6156. PMID 28590079.

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[1] Cope, Arthur C.; Shen, T. Y. (1956). "The Stereochemistry of 1,4: 3,6-Dianhydrohexitol Derivatives1". Journal of the American Chemical Society. 78 (13): 3177. doi:10.1021/ja01594a055.

[2] Le Nôtre, Jérôme; Van Haveren, Jacco; Van Es, Daan S. (2013). "Synthesis of Isoidide through Epimerization of Isosorbide using Ruthenium on Carbon". ChemSusChem. 6 (4): 693–700. doi:10.1002/cssc.201200714. PMID 23457114.

[3] Wu, Jing; Thiyagarajan, Shanmugam; Fonseca Guerra, Célia; Eduard, Pieter; Lutz, Martin; Noordover, Bart A. J.; Koning, Cor E.; Van Es, Daan S. (2017). "Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals". ChemSusChem. 10 (16): 3202–3211. doi:10.1002/cssc.201700617. hdl:1871.1/e9774e3a-858a-4003-97a6-4640b04b6156. PMID 28590079.