C. Falentin et al. / Tetrahedron 64 (2008) 9989–9991
9991
ꢁ
2
150 C; H NMR (300 MHz, D O): d
1
DMSO-d
for C BrO
6
):
d
171.9, 82.9, 73.8, 58.7, 44.3; ESIMS: m/z calcd [MþNa]þ
4.00 (t, 1H, J¼7.2 Hz), 3.85 (m,
13
5
H
7
4
: 234, found: 234.
1H), 3.67 (m, 2H), 3.57 (d, 1H, J¼3.6 Hz); C NMR (75 MHz, D
2
O):
þ
d
176.5, 72.9, 70.0, 62.5, 58.0; ESIMS: m/z calcd [MþNa] for
3
.1.3. 2-Azido-2-deoxy-
xylono-1,4-lactone (7)
To a solution of 2-bromo-2-deoxy-
930 mg, 14.3 mmol) in CH CN (10 mL) was added NaN
.95 mmoL). The mixture was refluxed for 6 h. Filtration and con-
D
-lyxono (6) and 2-azido-2-deoxy-
D-
C
5 5
H11NO : 188, found: 188.
D-xylono-1,4-lactone (5)
3.1.5.2. (ꢀ)-Polyoxamic acid (3). Yield 84 mg, 100%; white solid;
20 6c 1
ꢁ
ꢁ
(
8
3
3
(582 mg,
[a
]
D
ꢀ7 (c 0.22, water); mp 150–155 C; lit. mp 151–153 C;
H
NMR (300 MHz, D O): 3.86 (m,1H), 3.82 (dd,1H, J 2.3 Hz), 3.68 (m,
2
d
13
centration gave a residue, which was chromatographed (EtOAc/
cyclohexane, 4:6) to give the lyxo isomer (6) (240 mg, 32%) as col-
ourless oil; [
2H), 3.57 (d, 1H, J 5.4 Hz); C NMR (75 MHz, D
2
O):
d
178.5, 71.5,
: 188,
þ
71.0, 63.0, 58.2; ESIMS: m/z calcd [MþNa] for C
5
H
11NO
5
2
0
1
a]
D
þ38 (c 0.25, water); H NMR (300 MHz, D
2
O):
found: 188.
d
4.79 (dd, 1H, J¼4.8 Hz), 4.65 (d, 1H, J¼3.0 Hz), 4.61 (m, 1H), 3.86 (t,
13
2
5
H, J¼6.5 Hz); C NMR (75 MHz, D
2
O):
d
174.7, 82.9, 69.9, 62.2,
: 196, found: 196. The
þ
9.5; ESIMS: m/z calcd [MþNa] for C
5
H
7
N
3
O
4
Acknowledgements
xylo isomer (7) was then isolated (320 mg, 42%) as colourless solid;
2
0
ꢁ
12
ꢁ
1
[
a
]
D
þ142 (c 0.22, water); mp 80–82 C; lit. mp 80–82 C;
H
We thank the Minist e` re de la Recherche, the Conseil R e´ gional de
Picardie and the CNRS for financial support.
NMR (300 MHz, D O):
2
d
4.77 (d, 1H, J¼8.6 Hz), 4.70 (ddd, 1H,
13
J¼4.6 Hz), 4.60 (dd, 1H, J¼7.7 Hz), 3.91 (t, 2H, J¼3.0 Hz); C NMR
(
[
75 MHz, D
MþNa] for C
2
O):
d
174.2, 81.2, 71.5, 63.1, 58.7; ESIMS: m/z calcd
: 196, found: 196.
þ
H
7
N
3
O
4
References and notes
5
1
. (a) Suzuki, S.; Isono, K.; Mizutani, T.; Kawashima, Y.; Mizuno, T. J. Antibiot. 1965,
3
.1.4. General procedure for the preparation of 2-azido-2-deoxy-
lyxonic acid (8) and 2-azido-2-deoxy- -xylonic acid (9)
To a solution of 2-azido-2-deoxy- -pentonolactones (6 or 7)
D-
A18, 131–134; (b) Isono, K. J. Antibiot. 1988, 41, 1711–1739; (c) Isono, K. Phar-
macol. Ther. 1991, 52, 269–286; (d) Isono, K.; Suzuki, S. Heterocycles 1979, 13,
333–351 (review); (e) Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91,
D
D
7490–7505.
(
(
210 mg, 1.21 mmol) in 3:1 EtOH/water (2 mL) was added LiOH
1 equiv). The reaction mixture was stirred at room temperature for
2
3
. Hori, M.; Kakiki, K.; Misato, T. Agric. Biol. Chem. 1974, 38, 699–705.
. Shenbagamurthi, P.; Smith, H. A.; Becker, J. M.; Steinfeld, A.; Naider, F. J. Med.
Chem. 1983, 26, 1518–1522.
1
h and EtOH (2 mL) was added. The suspension was filtered and
the obtained white solid was washed with 3:1 EtOH/water (2 mL)
to give the desired 2-azido-2-deoxy- -aldonic acid lithium salt. A
solution of the obtained 2-azido-2-deoxy-
4
. (a) VanMiddlesworth, F.; Giacobbe, R. A.; Lopez, M.; Garrity, G.; Bland, J.;
Zweerink, M.; Edison, A. M.; Rozdilsky, W.; Wilson, K. E.; Monaghan, R. A.
J. Antibiot. 1992, 45, 861–867; (b) VanMiddlesworth, F.; Dufresne, C.; Wincott, F.
E.; Mosley, R. T.; Wilson, K. E. Tetrahedron Lett. 1992, 33, 297–300.
. Li, S.; Hui, X. P.; Yang, S. B.; Jia, Z. J.; Xu, P. F.; Lu, T. J. Tetrahedron: Asymmetry
D
D
-pentanoic acid lithium
þ
5
6
salt in water was treated with Amberlite IR-120H . The suspension
was stirred for 5 min at room temperature, the resin was filtered off
and the filtrate was concentrated under diminished pressure to
give the desired azido acid 8 or 9.
2005, 16, 1729–1731.
. (a) Collet, M.; G e´ nisson, Y.; Baltas, M. Tetrahedron: Asymmetry 2007, 18, 1320–
1329; (b) Enders, D.; Vrettou, M. Synthesis 2006, 13, 2155–2158; (c) Tarrade, A.;
Dauban, P.; Dodd, R. H. J. Org. Chem. 2003, 68, 9521–9524; (d) Kim, K. S.; Lee, Y.
J.; Kim, J. H.; Sung, D. K. Chem. Commun. 2002, 1116–1117; (e) Pepper, A. G.;
Procter, G.; Voyle, M. Chem. Commun. 2002, 1066–1067; (f) Bose, A. K.; Banik, B.
K.; Mathur; Wagle, C.; Dilip, R.; Manhas, M. S. Tetrahedron 2000, 56, 5603–5619;
(g) Uchida, K.; Kato, K.; Yamaguchi, K.; Akita, H. Heterocycles 2000, 53, 2253–
3.1.4.1. 2-Azido-2-deoxy-D-lyxonic acid (8). Yield 250 mg, 100%;
2
0
ꢁ
1
white solid; [
a
]
D
þ17 (c 0.34, water); mp 120–125 C; H NMR
2260; (h) Ghosh, A. K.; Wang, Y. Tetrahedron 1999, 55, 13369–13376; (i) Uchida,
(
2
300 MHz, D O): d
3.93 (d, 1H, J¼3.2 Hz), 3.71 (dd, 1H, J¼4.0 Hz),
K.; Kato, K.; Akita, H. Synthesis 1999, 1678–1686; (j) Ghosh, A. K.; Wang, Y. J. Org.
Chem. 1999, 64, 2789–2795; (k) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem.
Soc., Perkin Trans. 11999, 3291–3303; (l) Harwood, L. M.; Robertson, S. M. Chem.
Commun. 1998, 2641–2642; (m) Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39,
1
3
3
7
.64 (m, 1H),
d
3.57 (m, 2H); C NMR (75 MHz, D
2.2, 66.4, 62.5; ESIMS: m/z calcd [MþNa] for C
2
O):
d
175.2, 72.4,
þ
H N O : 214,
5 9 3 5
found: 214.
119–122; (n) Kang, S. H.; Choi, H. W. Chem. Commun. 1996, 1521–1523; (o) Trost,
B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520–
6521; (p) Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733–
735; (q) Chida, N.; Koizumi, K.; Kitada, Y.; Yokoyama, C.; Ogawa, S. J. J. Chem.
Soc., Chem. Commun. 1994, 111–113; (r) Jackson, R. F. W.; Palmer, N. J.; Wythes,
M. J. J. Chem. Soc., Chem. Commun. 1994, 95–96; (s) Casiraghi, G.; Passu, G.;
Spanu, P.; Pinna, L. Tetrahedron Lett. 1994, 35, 2423–2426; (t) Ariza, J.; Diaz, M.;
Font, J.; Ortuno, R. M. Tetrahedron 1993, 49, 1315–1326; (u) Dondoni, A.; Franco,
S.; Metchan, L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5475–5478; (v)
Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1993, 58, 307–309; (w)
Savage, L.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717–719; Garner, P.;
Park, J. M. J. Org. Chem. 1988, 53, 2979–2984; (x) Dureault, A.; Careaux, F.;
Depezay, J. C. Tetrahedron Lett. 1989, 30, 4527–4530; (y) Hirama, M.; Hioki, H.;
Ito, S. Tetrahedron Lett. 1988, 29, 3125–3128; (z) Saksena, A. K.; Lovey, R. G.;
Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024–5028.
3
.1.4.2. 2-Azido-2-deoxy-D-xylonic acid (9). Yield 248 mg, 100%;
20
ꢁ
1
white solid; [
a
O):
]
D
ꢀ31 (c 0.35, water); mp 190–194 C; H NMR
4.09 (d, 1H, J¼6.5 Hz), 3.88 (m, 1H), 3.86 (m,
(
1
(
[
300 MHz, D
H), 3.70 (dd, 1H, J¼5.0 Hz), 3.62 (dd, 1H, J¼11.0 Hz); C NMR
75 MHz, D O): 175.4, 71.0, 70.9, 66.5, 62.8; ESIMS: m/z calcd
MþNa] for C : 214, found: 214.
2
d
d
13
2
d
þ
5 9 3 5
H N O
3
.1.5. General procedure for the preparation of 3,4-diepipolyoxamic
acid (2) and (ꢀ)-polyoxamic acid (3)
To a solution of the obtained 2-azido-2-deoxy-D-pentanoic acid
(
100 mg, 0.52 mmol) in water (2.5 mL) was added palladium on
7. Chaveriat, L.; Stasik, I.; Demailly, G.; Beaup e` re, D. Tetrahedron 2004, 60, 2079–
081.
. Bouchez, V.; Stasik, I.; Beaup e` re, D.; Uzan, R. Tetrahedron Lett. 1997, 38,
733–7736.
9. Lalot, J.; Manier, G.; Stasik, I.; Demailly, G.; Beaup e` re, D. Carbohydr. Res. 2001,
35, 55–61.
0. Fleet, G. W. J. J. Chem. Soc., Perkin Trans. 1: Org. Bioorg. Chem. 1989, 3, 665–666.
1. Bock, K.; Lundt, I.; Pedersen, C. Carbohydr. Res. 1981, 90, 17–26.
12. Bols, M.; Lundt, I. Acta Chem. Scand. 1988, B42, 67–74.
2
charcoal (10%, 34 mg) and the suspension was hydrogenated for 2 h
at room temperature. The mixture was filtered through a layer of
Celite to give the desired 2-amino-2-deoxy-
8
7
D-pentanoic acid.
3
1
1
3
.1.5.1. 3,4-Diepipolyoxamic acid (2). Yield 85 mg, 100%; white
2
0
ꢁ
5
solid; [
a
]
D
þ12 (c 0.23, water); mp 142–145 C; lit. mp 145–