Abstract
Methyl l-sorboside monohydrate, C7H14O6·H2O, was prepared from the rare sugar l-sorbose, C6H12O6, and crystallized. It was confirmed that methyl l-sorboside formed α-pyran-ose with a 2 C 5 conformation and crystallized with one water molecule of crystallization. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming a three-dimensional network. The unit-cell volume of the title compound, methyl l-sorboside monohydrate, is 481.13 (2) Å3 (Z = 2), which is about 108.16 Å3 (29.0%) greater than that of half the amount of the chemical α-l-sorbose [745.94 (2) Å3 (Z = 4)].
Highlights
Methyl l-sorboside monohydrate, C7H14O6ÁH2O, was prepared from the rare sugar l-sorbose, C6H12O6, and crystallized
It was confirmed that methyl l-sorboside formed -pyranose with a 2C5 conformation and crystallized with one water molecule of crystallization
The unit-cell volume of the title compound, methyl l-sorboside monohydrate, is 481.13 (2) A 3 (Z = 2), which is about 108.16 A 3 (29.0%) greater than that of half the amount of the chemical -l-sorbose [745.94 (2) A 3 (Z = 4)]
Summary
The rare sugar l-sorbose was the first l-form hexose found in nature (Itoh et al, 1995; Khan et al, 1992; Nordenson et al, 1979). Methyl l-sorboside (Fig. 1) is an -pyranose form in which the OH group located on the C-2 position in l-sorbose is converted into a methoxy group OCH3. The molecular weight of methyl l-sorboside, C7H14O6ÁH2O, is 212.20. The increase in molecular weight from sorbose to sorboside is about 18%. We aimed to produce a single crystal of methyl l-sorboside that contains sorboside molecules and water molecules in the ratio of 1 to 1 in the unit cell. The crystal system of ethyl l-sorboside (Nagayama et al, 2020), which we reported previously, is orthorhombic, while that of methyl l-sorboside is triclinic. Concerning the crystal solvent, ethyl-l-sorboside contains no solvent molecules in the crystal, whereas crystals of methyl l-sorboside contain water molecules as crystallization water.
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