Table 1.

Summary of the syntheses of triacylated nicotinamide (or ethyl nicotinate) riboside salts 2,3,5-triacyl-NR⁺Xˉ (or 2,3,5-triacyl-NAR⁺Xˉ) and nicotinamide riboside salts NR⁺Xˉ.

starting reagents		glycosylation reaction conditions: solvent/temp/time, Lewis acid	deacylation reaction conditions	product and yield, %		ref.
Nam or derivative or analogue	sugar			2,3,5-triacyl- NAR+X−	β-NR+X−
1a	α/β-3a	MeCN/ 0 °C/42 h	NH3/MeOH, 0 °C, 18 h	α/β-4a, 62%	X = Cl, yield not given	[20]
1a	α/β-3b	MeCN/ 0 °C/36 h	NH3/MeOH, 0 °C, 18 h	α/β-4b, 40%	X = Cl, 73% (β/α ca. 4:1)	[20]
1a	α/β-5	MeCN/ rt/2 h	1 M NH3/MeOH, −15 °C, 4 days	6 (β/α ca. 4:1), 91%	X = Cl, 34% (ca. 85% of β)	[22]
1a	α/β-3a (ca. 94% of β)	MeCN/ 70 °C/20 min	1.25 M HCl/MeOH, rt, 12 h	α/β-4a, 62% (β/α ca. 6:4)	X = Cl, yield not given	[25]
1a	α/β-7b	MeCN/ −5 °C/48 h	–	β-8b, 61%	–	[22]
1a	α/β-7a	SO2/−10 °C/ overnight	–	β-8a, 96%	–	[26]
1a	α/β-7b	SO2/−10 °C/ overnight	NH3/MeOH, −18 °C, 72 h	β-8b, 90%	X = Br, 55%	[26]
1a	α/β-7a (β/α ca. 1.5:1)	SO2/−10 °C/ overnight	1 M NH3/MeOH, −5 °C, 20 h	β-8a, 90% (β/α ca. 25:1)	X = Br, 80%	[27]
1a	α/β-7a (β/α ca. 1.5:1)	MeCN/ −15 °C	–	β-8a, 65%	–	[27]
1a	β-2a	MeCN/rt/1 h, TMSOTf	MeOH, rt, 30 min	α/β-9a, yield not given	X = OTf, 58% (β/α 87:13)	[29]
10a	β-2a	DCE/45 °C/2 h, TMSOTf	NH3/MeOH, −5 °C, 6 h	β-9a, 96%	X = OTf, 45%	[30]
10a	β-2b	DCE/45 °C/2 h, TMSOTf	NH3/MeOH, −5 °C, 48 h	β-9b, 93%		[30]
1a	α/β-2a	MeCN/rt/1 h, TMSOTf	1 M MeONa/MeOH, 3−5 °C, 40 min	α/β-9a, yield not given	X = Cl (ion exchange), 34% (MeOH solvate)	[32]
14	β-2a	DCE/45 °C/8 h, TMSOTf	5.5 M NH3/MeOH, 0 °C, 15−18 h	β-17, >90%	X = OTf, 85%	[39]