Table 2.

Functionalizations of MDPM-protected uridines.

Entry	Starting material	Conditions	Product	Yield (%)a
1	10a : R = TBS 10b : R = Tr	NBS, TMSOTf/ CH3CN, rt, 1h	11a : R = TBS 11b : R = Tr	75 (95)b for 10a 90 (98)b for 10b
2	11a	50% HF/ CH3CN, rt, 1h	12	80
3	11b	BF3-OEt2 (3 equiv), TolSH/ CH2Cl2, rt, 1h	12	90
4	13	50% HF/ CH3CN, rt, 12h	8	88
5	8	TsOH-H2O/ acetone, rt, 4h	14	90
6	15	H2 (1 atom) / 10% Pd-C iPrOH-watert, 2h	14	95c
7	16	nBuSnH, AIBN / toluene, reflux, 2h	17	75
8	17	H2 (1 atom) / 10% Pd-C MeOH, 2h,	18	95c

^aProduct was isolated by SiO₂ chromatography or PTLC.,

^byield based on recovering starting material.,

^cno over-reduction was observed.