(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Electric Literature of C6H14O7
B3LYP/6-311++G** study of monohydrates of α- and β-D-glucopyranose: hydrogen bonding, stress energies, and effect of hydration on internal coordinates was written by Momany, F. A.;Appell, M.;Strati, G.;Willett, J. L.. And the article was included in Carbohydrate Research in 2004.Electric Literature of C6H14O7 This article mentions the following:
Twenty-six monohydrates of α- and β-D-glucopyranose were studied using gradient methods at the B3LYP/6-311++G level of theory. Geometry optimization was carried out with the water mols. at different configurations around the glucose mol. A new nomenclature for hydrated carbohydrates was developed to describe the water configurations. Zero-point vibrational energy, enthalpy, entropy, and relative free energy were obtained using the harmonic approximation Hydrogen-bond energies for the monohydrates range from ∼-5 to -12 kcal/mol, and the average relative free energy is ∼5 kcal/mol. The 1-hydroxy position is the most energetically favored site for hydration, and the region between the two and three positions is the next-most favored site. A water mol. approaching α-D-glucose between the 1- and 2-hydroxy positions pulls the 2-hydroxyl hydrogen atom away from the 1-hydroxy oxygen atom, thus increasing the hydrogen-bond length and also increasing the α-D-glucose energy. The increase in energy that occurs with a similar interaction on the β-anomer is much less effective since the hydrogen bond is much longer. Using the calculated free energies of all 26 configurations, the anomer population (α/β) increases in the β-anomer population relative to the in vacuo case by ∼10% at the expense of the α-anomer, giving an (α/β) ratio of ∼50/50. This result arises from entropy contributions favoring the β-anomer more than the α-anomer. From anal. of donor and acceptor hydrogen-bond lengths, excellent correlation is found between the DFT calculated distances and those taken from carbohydrate structures in the Cambridge Crystallog. Data Bank. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7Electric Literature of C6H14O7).
(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Electric Literature of C6H14O7
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics