Aldono-1,5-lactone → 1-C-(1,3-dithian-2-yl)-D-glucopyranose

Participants

Reaction Steps

Process 1", i.e. a process to produce, for example, 1-C-[bis(methylthio)methyl]-D-glucopyranose derivative (2") from D-glucono-δ-lactone derivative (1"), is conducted by allowing the compound (1") to react with bis(methylthio)methyllithium, or a process to produce 1-C-(1,3-dithian-2-yl)-D-glucopyranose (2"), is conducted by allowing the compound (1") to react with 2-lithio-1,3-dithiane. In this reaction, usually 1 to 5 mole equivalents, preferably 2-2.5 mole equivalents, of bis(methylthio)methyllithium or 2-lithio-1,3-dithiane for D-glucono-δ-lactone derivative (1") is used. This reaction is conducted in an appropriate solvent which is inactive to this reaction, such as tetrahydrofuran, 1,4-dioxane, ethyl ether, and hexane, which are used separately or in combination, preferably in an atmosphere of an inert gas such as nitrogen and argon. Reaction temperature is usually -20° C. --78° C., preferably -50° C.--78° C. in the initial stage of the reaction and -20° C.--40° C. in the later stage. Reaction time is appropriately about 1-8 hours.

Provenance & Evidence