References and Notes
1a
Heightman TD.
Vasella AT.
Angew. Chem. Int. Ed.
1999,
38:
750
1b
Sears P.
Wong C.-H.
Angew. Chem. Int. Ed.
1999,
38:
2301
1c
Davies JA.
Fisher CE.
Barnett MW.
Biochem. Soc. Trans.
2001,
29:
166
2a
Simmott ML.
Chem. Rev.
1990,
90:
1171
2b
Barbier P.
Stadlwieser J.
Taylor S.
Science
1998,
280:
1369
3
Ishida N.
Kumagai K.
Niida T.
J.
Antibiot. [A]
1967,
20:
66
4
Papandreou M.-J.
Barbouche R.
Guieu R.
Kieny MP.
Fenouillet E.
Molec.
Pharmacol.
2002,
61:
186
5a
Martin OR. In Carbohydrate
Mimics: Concepts and Methods
Chapleur Y.
VCH;
Weinheim:
1998.
p.259
5b
Li H.
Blériot Y.
Chantereau C.
Mallet J.-M.
Sollogoub M.
Zhang Y.
Rodriguez-Garcia E.
Vogel P.
Jimenez-Barbero J.
Sinay P.
Org. Biomol. Chem.
2004,
2:
1492
5c
Dhavale DD.
Markad SD.
Karanjule NS.
PrakashaReddy J.
J.
Org. Chem.
2004,
69:
4760
6a
Andreana PR.
Sanders T.
Janczuk A.
Warrick JI.
Wang PG.
Tetrahedron Lett.
2002,
43:
6525
6b
Moutel S.
Shipman M.
Martin OR.
Ikeda K.
Asano N.
Tetrahedron:
Asymmetry
2005,
16:
487
6c
Li H.-Q.
Liu T.
Zhang YM.
Favre S.
Bello C.
Vogel P.
Butters
TD.
Oikonomakos NG.
Marrot J.
Bleriot Y.
ChemBioChem.
2008,
9:
253
7
Kuszmann J.
Sohár P.
Carbohydr. Res.
1979,
74:
187
8a
Kato L.
Dissertação
de Mestrado
Universidade de Campinas;
Brazil:
1996.
8b
Kato L.
Braga RM.
Magn. Reson. Chem.
1999,
37:
447
8c
Braga RM.
Kato L.
J. Braz. Chem.
Soc.
2003,
14:
822
9
Spectroscopic Data
for (5
S
)-Amino-(4
R
)-
O
-benzyl-1,5,6-trideoxy-(2
S
,3
R
)-
O
-isopropylidene-1,6-imino-
d
-glucitol (16,
Figure 2)
R
f
= 0.2 (CHCl3-MeOH,
9:1; 2×). IR (KBr): 3360, 3291 (NH), 2851 (CH), 1070 (CN)
cm-¹. MS: m/z (%) = 57 (16), 71
(21), 84 (26), 91 (100), 98 (49), 110 (8), 126 (34), 141 (7), 149
(10), 167 (14), 184 (27), 201 (23), 227 (3), 277 (10), 292 (2). ¹H
NMR (500 MHz, CDCl3): δ = 1.43, 1.44 [6
H, 2 s, C(CH3)2], 2.13-2.18
(3 H, br s, NH aliphatic and cyclic), 2.71 (1 H, dd, ²
J = 11.7 Hz, ³
J = 9.0 Hz,
H1-α), 2.81 (1 H, dd, ²
J = 14.4 Hz, ³
J = 6.8 Hz,
H6-α), 2.89 (1 H, dd, ²
J = 14.4 Hz, ³
J = 2.2 Hz,
H6-β), 3.00 (1 H, ddd, ³
J = 6.8 Hz, ³
J = 4.6 Hz, ³
J = 2.2 Hz,
H5), 3.37 (1 H, dd, ³
J = 9.0
Hz, ³
J = 4.6
Hz, H4), 3.40 (1 H, dd, ²
J = 11.7 Hz, ³
J = 4.8 Hz,
H1-β), 3.89 (1 H, td, ³
J = 9.0 Hz, ³
J = 4.8 Hz,
H2), 4.01 (1 H, t, ³
J = 9.0 Hz,
H3), 4.68 (1 H, d, ²
J = 11.7
Hz, OCHH′C6H5), 4.93 (1 H, d, ²
J = 11.7 Hz,
OCHH′C6H5), 7.29 (1 H, t, ³
J = 7.4 Hz,
H4′), 7.35 (2 H, t, ³
J = 7.4
Hz, H3′, H5′), 7.39 (2 H, d, ³
J = 7.4 Hz, H2′,
H6′). ¹³C NMR (125 MHz, CDCl3): δ = 27.0,
27.2 [C(CH3)2], 49.2 (C6),
49.8 (C1), 55.9 (C5), 72.9 (OCH2C6H5),
75.9 (C2), 83.4 (C3), 85.8 (C4), 109.2 [C(CH3)2],
127.6 (C4′), 128.0 (C2′, C6′), 128.3
(C3′, C5′), 138.6 (C1′).