ORDER
REPRINTS
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Glac¸on et al.
20.4 (CH3); 1H NMR (CDCl3): d 5.06 (m, 2H, H-2,3), 3.33 (dd, 2H, J1 ,2, J3,4
0
0
4.5 Hz, H-10,40), 3.26 (dd, 2H, J1,2, J3,4 7.2 Hz, J1,1 , J4,4 13.3 Hz, H-1,4), 2.00, 1.97 (2s,
6H, CH3).
0
0
Anal. Calcd for C8H12N6O4: C, 37.50; H, 4.72; N, 32.80; O, 24.98. Found: C, 37.93;
H, 4.62; N, 32.14.
2,3,4-Tri-O-acetyl-1,5-diazido-1,5-dideoxyxylitol (14). Reaction of crude product
obtained from 12 according to GPII followed by GPIII gave 14 after chromatography on
silica gel (9 : 1 hexane–AcOEt). 14 (1.62 g, 75%); colorless crystals; m.p. 54–558C; Rf
0.40 in 8 : 2 hexane–AcOEt; 13C NMR (CDCl3): d 169.8, 169.7 (CO), 69.9 (C-2,4),
1
69.7 (C-3), 50.7 (C-1,5), 20.5, 20.4 (CH3); H NMR (CDCl3): d 5.30 (t, 1H, J2,3, J3,4
0
0
5.2 Hz, H-3), 5.05 (m, 2H, J1,2, J4,5 5.8 Hz, H-2,4), 3.40 (dd, 2H, J1 ,2, J4,5 4.1 Hz,
H-10,50), 3.32 (dd, 2H, J1,1 , J5,5 13.2 Hz, H-1,5), 2.10, 2.00 (2s, 3H, 6H, CH3).
Anal. Calcd for C11H16N6O6: C, 40.25; H, 4.91; N, 25.60; O, 29.24. Found: C, 40.53;
H, 4.61; N, 25.71.
0
0
2,3,4,5-Tetra-O-acetyl-1-azido-1-deoxy-D,L-xylitol (16). Yield 0.23 g (10%);
syrup; Rf 0.60 in 6 : 4 hexane–AcOEt; 13C NMR (CDCl3): d 170.0, 169.8 (CO), 69.8
1
(C-2), 69.2 (C-3), 68.5 (C-4), 61.6 (C-5), 50.1 (C-1), 20.3, 20.1, 19.9 (CH3); H NMR
(CDCl3): d 5.30 (dd, 1H, J2,3 5.0, J3,4 5.3 Hz, H-3), 5.10 (ddd, 1H, H-4), 5.01 (ddd, 1H,
H-2), 4.22 (dd, 1H, J4,5 4.0 Hz, J5,5 12.2 Hz, H-50), 3.89 (dd, 1H, J4,5 6.3 Hz, H-5),
0
0
3.38 (dd, 1H, J1 ,2 4.3, J1,1 13.5 Hz, H-10), 3.33 (dd, 1H, J1,2 6.0 Hz, H-1), 2.00, 1.97,
1.95, 1.93 (4s, 12H, CH3).
0
0
Anal. Calcd for C13H19N3O8: C, 45.22; H, 5.55; N, 12.17; O, 37.07. Found: C, 45.33;
H, 5.64; N, 12.51.
2,3-Di-O-acetyl-1,4-anhydro-5-azido-5-deoxy-D,L-xylitol (18). Yield 0.18 g
(11%); syrup; Rf 0.35 in 8 : 2 hexane–EtOAc; 13C NMR (CDCl3): d 168.6 (CO), 77.4
1
(C-4), 76.3 (C-2), 75.2 (C-3), 70.7 (C-1), 48.7 (C-5), 19.7 (CH3); H NMR (CDCl3): d
5.00 (dd, 1H, J2,3 0.6 Hz, J3,4 3.6 Hz, H-3), 4.84 (m, 1H, H-2), 3.98 (dd, 1H, H-4), 3.85
(dd, 1H, J1 ,2 4.8 Hz, J1,1 10.8 Hz, H-10), 3.50 (dd, 1H, J1,2 2.0 Hz, H-1), 3.30 (m, 2H,
0
0
J5,5 11.9 Hz, H-5,50), 1.89, 1.85 (2s, 12H, CH3).
0
Anal. Calcd for C9H13N3O5: C, 44.44; H, 5.39; N, 17.28; O, 32.89. Found: C, 44.53;
H, 5.73; N, 17.62.
2,3,4-Tri-O-acetyl-1,5-diazido-1,5-dideoxyribitol (22). Reaction of crude product
obtained from 20 according to GPII followed by GPIII gave 22 after chromatography on
silica gel (9 : 1 hexane–AcOEt). 1.25 g (58%); syrup; Rf 0.42 in 8 : 2 hexane–AcOEt; 13
NMR (CDCl3): d 169.8, 169.3 (CO), 69.5 (C-2,4), 69.3 (C-3), 49.4 (C-1,5), 19.7, 19.6
C
1
(CH3); H NMR (CDCl3): d 5.23 (m, 2H, H-2,4), 5.13 (t, 1H, J2,3, J3,4 5.2 Hz, H-3),
3.48 (dd, 2H, J1 ,2, J4,5 3.5 Hz, H-10,50), 3.37 (dd, 2H, J1,2, J4,5 6.4 Hz, J1,1 , J5,5
13.5 Hz, H-1,5), 2.07, 2.05 (2s, 6H, 3H, CH3).
0
0
0
0
Anal. Calcd for C11H16N6O6: C, 40.25; H, 4.91; N, 25.60; O, 29.24. Found: C, 40.63;
H, 4.51; N, 25.65.
2,3,4,5-Tetra-O-acetyl-1-azido-1-deoxy-D,L-ribitol (24). Yield 0.23 g (10%);
syrup; Rf 0.63 in 6 : 4 hexane–EtOAc; 13C NMR (CDCl3): d 170.2, 169.7, 169.5 (CO),
1
70.1 (C-2), 69.5 (C-3), 69.2 (C-4), 61.3 (C-5), 49.7 (C-1), 20.7, 20.6, 20.5 (CH3); H
NMR (CDCl3): d 5.25 (ddd, 1H, J2,3 5.2 Hz, J3,4 5.3 Hz, H-3), 5.15 (m, 1H, H-4), 5.05
(m, 1H, H-2), 4.20 (dd, 1H, J4,5 3.0, J5,5 12.5 Hz, H-50), 3.99 (dd, 1H, J4,5 6.0 Hz,
0
0
H-5), 3.41 (dd, 1H, J1 ,2 3.5 Hz, J1,1 13.2 Hz, H-10), 3.30 (dd, 1H, J1,2 6.9 Hz, H-1),
2.05, 2.00 (2s, 6H, 6H, CH3).
0
0