I. A. S. Smellie et al. / Tetrahedron Letters 52 (2011) 95–97
97
R
R
O
NO2
O
NOH
Cl
a,b
AcO
AcO
4 R = H
AcO
R1
AcO
AcO
OAc
AcO
OAc
O
N
3 R = H
OH
10 R = CH2OAc
12 R = CH2OAc
AcO HN
e
OAc
OAc
O
c
R2
R
R
OAc
O
O
NH2.HCl
d
17 R1 = R2 = H
AcO
CN
AcO
AcO
18 R1 = H, R2 = CH2OAc
19 R1 = CH2OAc, R2 = H
20 R1 = R2 = CH2OAc
AcO
OAc
OAc
15 R = H
13 R = H
16 R = CH2OAc
14 R = CH2OAc
Scheme 3. Reagents and conditions: (a) PhSH, Et3N, SnCl2, THF, 0 °C; (b) Cl2, CH2Cl2, ꢀ78 °C; (c) PCl3, pyridine; (d) H2, 10% PtO2, EtOH–5% CHCl3; (e) Et3N.
14. Baker, K. W. J.; Horner, K. S.; Moggach, S. A.; Paton, R. M.; Smellie, I. A. S.
Tetrahedron Lett. 2004, 45, 8913–8916.
References and notes
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16. Baker, K. W. J.; Gibb, A.; March, A. R.; Parsons, S.; Paton, R. M.; Stewart, G. W.
Synth. Commun. 2003, 33, 1707–1715.
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18. (Z)-N-(6-Deoxy-1,2:3,4-di-O-isopropylidene-
a
-
D-galactopyranosyl)-C-(2,3,4-
tri-O-acetyl-b-
D-xylopyranosyl)formamide oxime (1); white solid (81%); mp
ꢁ
167–168 °C; ½a 2D0
ꢀ74 (c = 1.0, CHCl3); dH (360 MHz, CDCl3) 1.33, 1.38, 1.49,
1.53 (12H, 4 ꢂ s, CH3), 1.97, 2.04, 2.05 (9H, 3s, COCH3), 3.33 (1H, dd, 5a-H),
3.34–3.59 (2H, m, 6a0-H, 6b0-H), 3.84–3.89 (1H, m, 50-H), 4.00 (1H, d, 1-H), 4.15
(1H, dd, 5e-H), 4.29–4.34 (2H, m, 20-H, 40-H), 4.63 (1H, dd, 30-H), 5.04 (1H, ddd,
4-H), 5.20 (1H, dd, 3-H), 5.24 (1H, m, NH), 5.40 (1H, dd, 2-H), 5.53 (1H, d, 10-H),
7.76 (1H, br s, OH); J(xꢀy)/Hz 1–2 10.1, 2–3 9.4, 3–4 9.4, 4–5a 9.0, 4–5e 5.4, 5a–
5e 11.2, 10–20 5.0, 20–30 2.5, 30–40 7.9; dC (93 MHz, CDCl3) 20.6 (COCH3), 24.3,
24.8, 25.8, 25.9 (ketal CH3), 42.6 (C-60), 66.7 (C-5), 67.4, 68.6, 68.7, 70.4, 70.6,
70.9, 73.7, 76.2 (C-1, C-2, C-3, C-4, C-20, C-30, C-40, C-50), 96.1 (C-10), 108.6, 109.3
(ketal C), 149.0 (C@N), 169.3, 169.7, 170.2 (COCH3); FAB-HRMS [M+H]+
calculated for C24H37N2O13: 561.2292; found: 561.2282.
19. CCDC no. 782624.
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22. For example: (Z)-N-(3,4,5-tri-O-acetyl-b-
D
-xylopyranosylmethyl)-(2,3,4,6-
oxime (18,
R1 = H,
ꢀ36 (c = 1.0, CHCl3);
tetra-O-acetyl-b-D-glucopyranosyl)formamide
R2 = CH2OAc); white solid (40%); mp 141–143 °C; ½a 2D0
ꢁ
dH (600 MHz, CDCl3) 1.93, 1.95, 1.98, 1.99, 2.00, 2.03, 2.04 (21H, 7 ꢂ s, COCH3),
3.17 (1H, ddd, 1a0-H), 3.26 (1H, dd, 6a0-H), 3.43 (1H, ddd, 20-H), 3.54 (1H, ddd,
1b0-H), 3.64 (1H, ddd, 5-H), 4.03 (1H, d, 1-H), 4.04–4.07 (1H, m, 6a-H), 4.09 (1H,
m, 6e0-H), 4.14 (1H, dd, 6b-H), 4.85 (1H, dd, 30-H), 4.89–4.93 (1H, m, 50-H), 4.95
(1H, dd, 4-H), 5.14–5.19 (2H, m, 40-H, 3-H), 5.25 (1H, dd, 2-H), 5.34 (1H, dd,
NH); J(xꢀy)/Hz 1–2 10.2, 2–3 9.6, 3–4 9.7, 4–5 9.9, 5–6a 2.2, 5–6b 5.8, 6a–6e
12.4, 1a0–20 6.6, 1b0–20 2.6, 1a0–1b0 11.1, 20–30 9.6, 30–40 9.6, 40–50 9.9, 50–6a0
10.9, 50–6e0 5.8, 6a0–6e0 11.2; dC (93 MHz, CDCl3) 20.4, 20.5, 20.6 (COCH3), 43.2
(C-10), 62.2 (C-6), 65.2 (C-60), 68.0, 68.2, 68.9, 70.0, 73.1, 73.8, 75.1, 75.9, 77.5
(C-1, C-2, C-3, C-4, C-5, C-20, C-30, C-40, C-50), 147.8 (C@N), 169.3, 169.7, 170.1,
170.4 (COCH3); FAB-HRMS: [M+H]+ calculated for C27H39N2O17: 663.2249;
found: 663.2250.
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