4
984
M. Murata et al. / Tetrahedron Letters 44 (2003) 4981–4984
8. (a) Aoi, K.; Motoda, A.; Ohno, M.; Tsutsumiuchi,
References
. Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis, 3rd ed.; John Wiley and Sons, Inc: New
York, 1999.
. (a) Bodanszky, M.; Bodanszky, A. The Practice of Peptide
Synthesis; Springer: Berlin, 1984; p. 153; For recent exam-
ples of the hydrogenolysis using Pd/C catalyst, see: (b)
Jost, M.; Greie, J.-C.; Stemmer, N.; Wilking, S. D.;
Altendorf, K.; Sewald, N. Angew. Chem., Int. Ed. 2002, 41,
K.; Okada, M.; Imae, T. Polym. J. 1999, 30, 1071; (b)
Aoi, K.; Ito, K.; Okada, M. Macromolecules 1997, 30,
8072.
1
2
9. Core-Z-protected poly(amido amine) dendrimer 1 was syn-
8
thesized by the divergent method according to literature.
Characterizations of 1 and the amino product 2 were as
follows. 1: IR (KBr) 3080 (wNꢀH), 2958, 2928, 2856 (wCꢀH),
1
1
654 (wCꢁO, amide), 1560 (lNꢀH, amide). H NMR (400
MHz, DMSO, TMS, 40°C) l 7.42 (br, NH), 7.34 (br,
4
267; (c) Chibale, K.; Chipeleme, A.; Warren, S. Tetra-
NH), 7.08–6.92 (m, aromatic CH of Z), 5.08 (s, CH of Z),
2
hedron Lett. 2002, 43, 1587; (d) Li, J.; Jeong, S.; Esser, L.;
Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765; (e)
Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S.
F. J. Am. Chem. Soc. 2001, 123, 5918; (f) Nakamura, H.;
Fujiwara, M.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000,
3
.20 (br, NHCH CH N), 3.17 (m, CH (CH ) CH ), 2.68
2 2 2 2 4 3
(
br, NCH CH CONH), 2.55 (m, NHCH CH N), 2.31 (br,
2 2 2 2
NCH CH CONH), 1.48 (m, CH (CH ) CH ), 1.28 (m,
2
2
2
2 3
3
13
(
CH ) CH ), 0.88 (m, (CH ) CH ). C NMR (400 MHz,
2 3 3 2 5 3
DMSO, TMS, 40°C) l 172.3 (CONH), 156.6 (CONH of
Z), 136.7 (quaternary aromatic carbon of Z), 128.3–127.8
7
3, 231.
3
. Bodanszky, M.; Ondetti, M. A.; Levine, S. D.; Williams,
N. J. J. Am. Chem. Soc. 1967, 89, 6753.
(
aromatic carbon), 66.4 (CH of Z), 52.6 (NHCH CH N),
2 2 2
5
1.3 (NCH CH CONH), 39.5 (CH (CH ) CH ), 37.7
2 2 2 2 3 3
4
. For typical examples of the deprotection with homoge-
neous acids, see: trifluoroacetic acid/thioanisole: (a)
Asayama, S.; Maruyama, A.; Akaike, T. Bioconjugate
Chem. 1999, 10, 246; p-TsOH; (b) VanNieuwenhze, M. S.;
Mauldin, S. C.; Zia-Ebrahimi, M.; Winger, B. E.; Horn-
back, W. J.; Saha, S. L.; Aikins, J. A.; Blaszczak, L. C. J.
Am. Chem. Soc. 2002, 124, 3656; HBr/AcOH; (c) Becerril,
J.; Burguete, M. I.; Escuder, B.; Luis, S. V.; Miravet, J. F.;
Querol, M. Chem. Commun. 2002, 738.
. Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani,
K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
. Sugiyama, S.; Minami, T.; Hayashi, H.; Tanaka, M.;
Shigemoto, N.; Moffat, J. B. J. Chem. Soc., Faraday
Trans. 1996, 92, 293.
(
NHCH CH N), 34.4 (NCH CH CONH), 31.7 (CH -
2 2 2 2 2
(
CH ) CH ), 29.6 (CH (CH ) CH ), 26.7 (CH CH CH ),
2 3 3 2 2 2 3 2 2 3
2
2.6 (CH CH ), 14.0 ((CH ) CH ). 2: IR (KBr) 3080
2
3
2 5
3
(
w
), 2929, 2857 (wCꢀH), 1647 (w
amide), 1559 (lNꢀH
,
NꢀH
CꢁO,
1
amide). H NMR (400 MHz, DMSO, TMS, 40°C) l
.81–7.73 (br, NH), 3.16 (br, NHCH CH N), 3.01 (m,
7
2
2
CH (CH ) CH ), 2.65 (br, NCH CH CONH), 2.44 (m,
2
2 4
3
2
2
NHCH CH N), 2.18 (br, NCH CH CONH), 1.38 (m,
2
2
2
2
5
CH
CH
2
(CH
2
)
3
CH ), 1.24 (m, (CH ) CH ), 0.86 (m, (CH ) -
3 2 3 3 2 5
13
). C NMR (400 MHz, DMSO, TMS, 40°C) l 170.9
CH N), 49.6 (NCH CH CONH),
), 36.8 (NHCH CH N), 33.2 (NCH
CH CONH), 30.8 (CH (CH ) CH ), 29.0 (CH (CH ) -
3
6
(CONH), 52.0 (NHCH
39.3 (CH (CH CH
2
2
2
2
)
2
-
2
2
3
3
2
2
2
2
2 3
3
2
2 2
7. Felix, A. M.; Heimer, E. P.; Lambros, T. J.; Tzougraki,
CH ), 26.0 (CH CH CH ), 21.9 (CH CH ), 13.7 ((CH ) -
3
2
2
3
2
3
2 5
C.; Meienhofer, J. J. Org. Chem. 1978, 43, 4194.
CH3).