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. Author manuscript; available in PMC: 2013 Jun 17.
Published in final edited form as: Tetrahedron. 2012 Apr 9;68(24):4797–4804. doi: 10.1016/j.tet.2012.03.121

Table 1.

Protection of the uridine ureido nitrogen with 1 and its relativities against representative reagents.

graphic file with name nihms367605u3.jpg
Conditionsa 8 (t1/2) Conditionsa 8 (t1/2)
20% TFA, CH2Cl2 >6h DBU, Toluene >24h
10% TMSOTf, CH2Cl2 >2h Al(Hg), 1,4-Dioxane >12h
10% HCl, MeCN >6h Raney Ni 1,4-Dioxane >12h
10% HCl, 1,4-dioxane >6h nBu3SnH, AIBN Toluene, reflux >6h
30% HF, MeCN >12h NBS
THF		 >6h
80% AcOH >12h
30% TsOH, 1,4-dioxane >12h hv, MeCN >6h
La(OTf)3, THF >12h H2/Pd-C, 1 atom MeOH >12hb
10% BF3-OEt2, CH2Cl2 >12h H2/Pd-C, 50 psi MeOH >12hb
10% TiCl4, CH2C12 >4h H2/Pd-C, 100 psi MeOH >12hb
DDQ, CH2Cl2-water >12h H2/Pd black MeOH >12hb
a

Reaction was carried out at room temperature.,

b

the uracil double bond of 8 was reduced.