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. 2012 Mar 26;68(21):4003–4012. doi: 10.1016/j.tet.2012.03.066

Table 2.

Oxidation of the HPMP analogues 8 with TEMPO/NaClO2/NaClO to give 9, followed by diester removal to yield 7

Entry Nucleobase B Starting compound Product (yield)a of oxidation Product (yield)a of the phosphonate deprotection
1 graphic file with name fx2.gif 8a (S)- 9a (87%) 7a (68%),b (46%)c
2 8b (R)- 9b (76%) 7b (50%)b
3 graphic file with name fx3.gif 8c (S)- 9c (83%) 7c (62%),b (39%)c
4 graphic file with name fx4.gif 8d (S)- 9d (82%) 7dd (64%),b (44%)c
5 graphic file with name fx5.gif 8e (S)- 9e (81%) 7e (42%)c
6 8f (R)- 9f (80%) 7f (48%)c
7 graphic file with name fx6.gif 8g (S)- Complex mixture (no 9g isolated)e 7g (61%),b (37%)c
8 graphic file with name fx7.gif 8h (S)- Complex mixture (no 9h isolated) 7h (38% from 9j)c,f
9 graphic file with name fx8.gif 8i (S)- 9i (78%) 7i (52%)b
10 graphic file with name fx9.gif 8j (S)- 9j (80%) N.A.g
a

Isolated yield.

b

Method A.

c

Method B.

d

Compound 7d contains thymine as a base.

e

Compound 9g prepared from 9i (Scheme 3).

f

Compound 7h prepared from 9j (Scheme 4).

g

N.A. not applicable.