X. Yin, S. W. Schneller / Tetrahedron Letters 46 (2005) 7535–7538
7537
OH
I
RO
RO
a
OAc
TBSO
OH
BnO
N3
BnO
N3
b
c
e
f
on 19
on 22
O
O
O
O
O
O
7, R=H5
O
O
19, R=TBS6b
20
21, R=H
22, R=Bn
23
25
d
g
h
Cl
N
N
O
N
F
F
BnO
N3
j
N
i
N
HO
4
BnO
O
O
O
HO
OH
O
O
26
24
27
OH
HO
OAc
O
k
m
l
5
75
O
O
O
O
29
28
Scheme 2. Reagents and conditions: (a) TBSCl, imidazole, CH2Cl2, 91%; (b) (i) OsO4, NMO, acetone/H2O; (ii) Me2C(OMe)2, acetone, pTSA, 90%
for two steps; (iii) NH3, MeOH, 85%; (c) (i) TPP, DIAD, toluene, 80 °C, 93%; (ii) TBAF, THF, 95%; (d) BnBr, NaH, DMF, 97%; (e) (i) HCl, MeOH;
(ii) mCPBA, CH2Cl2; (iii) NaN3, DMF/H2O; (iv) Me2C(OMe)2, acetone, pTSA, 59% for four steps; (f) (i) Tf2O, pyridine, CH2Cl2; (ii) LiI, THF 92%
for two steps; (g) (i) H2, Pd/C, MeOH, 90%; (ii) phthalic anhydride, Ac2O, pyridine; (iii) Pd(OH)2/C, cyclohexene, EtOH, 56% for two steps; (h) (i)
Tf2O, pyridine, CH2Cl2; (ii) TASF, THF, 77% for two steps; (i) (i) Lindlar catalyst, H2, MeOH; (ii) 5-amino-4,6-dichloropyrimidine, Et3N, 1-BuOH;
(iii) (EtO)2CHOAc, reflux, 35% for three steps;2b (j) (i) NH3, MeOH, 75%; (ii) Pd(OH)2/C, cyclohexene, EtOH, 100%; (iii) 1 N HCl, MeOH, 96%;2b
(k) Ref. 17; (l) Refs. 5c and 7; (m) steps (d), (e), (h), (i), and (j).
purine construction process2b,14 (Scheme 2, step i) to
Turmel, B. Tetrahedron Lett. 2004, 45, 739–742; (f)
Takagi, C.; Sukeda, M.; Kim, H. S.; Wataya, Y.; Yabe,
S.; Kitade, Y.; Matsuda, A.; Shuto, S. Org. Biomol. Chem.
2005, 3, 1245–1251.
provide 27. Ammonolysis, debenzylation and then
deisopropylidenation yielded 4.15
3. (a) Borthwick, A. D.; Kirk, B. E.; Biggadike, K.; Exall, A.
Enantiomer 516 was prepared from 28 using a procedure
M.; Butt, S.; Roberts, S. M.; Knight, D. J.; Coats, J. A. V.;
Ryan, D. M. J. Med. Chem. 1991, 34, 907–914; (b)
similar to that for obtaining 4.
Nakayama, T.; Matsumura, Y.; Morizawa, Y.; Yasuda,
The biological analysis of 3–5 is underway and will be
presented in the full paper on this class of nucleoside
derivatives.
A.; Uchida, K.; Takase, H.; Murakami, Y.; Atarashi, S.;
Ikeuchi, T.; Osada, Y. Chem. Pharm. Bull. 1994, 42, 183–
187; (c) Jeong, L. S.; Moon, H. R.; Park, J. G.; Shin, D.
H.; Choi, W. J.; Lee, K. M.; Kim, H. O.; Chun, M. W.;
Kim, H. D.; Kim, J. H. Nucleosides Nucleotides Nucleic
Acids 2003, 22, 589–592; (d) Yang, Y. Y.; Meng, W. D.;
Qing, F. L. Org. Lett. 2004, 6, 4257–4259; (e) Rosen, T.
C.; De Clercq, E.; Balzarini, J.; Haufe, G. Org. Biomol.
Chem. 2004, 2, 229–237; (f) Kim, H. O.; Yoo, S. J.; Ahn,
H. S.; Choi, W. J.; Moon, H. R.; Lee, K. M.; Chun, M.
W.; Jeong, L. S. Bioorg. Med. Chem. Lett. 2004, 14, 2091–
2093; (g) Moon, H. R.; Lee, H. J.; Kim, H. R.; Lee, K. M.;
Lee, S. K.; Kim, H. O.; Chun, M. W.; Jeong, L. S. Bioorg.
Med. Chem. Lett. 2004, 14, 5641–5644.
Acknowledgements
This research was supported by funds from the NIH (AI
56540).
References and notes
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