Methods of preparing reduced nicotinamide riboside and derivatives thereof

A method of making a compound of formula (IVA), or a salt, or a solvate thereof:

• the method comprising the steps of:
• (a) providing a compound of formula (IIIA)
• wherein n is 0 or 1;
• Y is O or S;
• m is 1;
• R1 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted primary or secondary amino, and azido;
• R2-R5 are each H;
• and
• R6, R7 and R8 are each independently selected from the group consisting of hydrogen, an ester-type protecting group, an ether-type protecting group, and a silyl protecting group;
• (b) oxidizing the compound of formula (IIIA) to provide a compound of formula (IVA)
• wherein X− is an anion selected from the group consisting of a halide, an anion of a substituted or unsubstituted monocarboxylic acid, an anion of a substituted or unsubstituted dicarboxylic acid, an anion of a substituted or unsubstituted phosphate, an anion of a substituted or unsubstituted sulfate, an anion of a substituted or unsubstituted carbonate, and an anion of a substituted or unsubstituted carbamate;
• (c) processing the compound of formula (IVA);
• and
• (d) isolating the compound of formula (IVA).