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DOI: 10.1055/s-0029-1219932
Solid-Phase Synthesis of Allosamidin
Publikationsverlauf
Publikationsdatum:
10. Mai 2010 (online)
Abstract
The solid-phase synthesis of allosamidin is described. After the NHCbz trichloroacetimidate donors were synthesized, solid-phase synthesis was performed using the Wang resin as support. The target allosamidin was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.
Key words
allosamidin - solid-phase synthesis - trichloroacetimidate donors - Wang resin - glycosylation reactions
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References and Notes
Allosamidin 1
IR
(KBr): 3500, 3365, 1652, 1550, 1060 cm-¹. ¹H
NMR (300 MHz, D2O): δ = 5.37 (dd, 1
H, H-1), 4.80 (d, 1 H, H-1′′), 4.78 (d, 1 H, H-1′),
4.37 (dd, 1 H, H-2), 4.36 (t, 1 H, H-3′), 4.30 (t, 1 H,
H-3), 4.07 (t, 1 H, H-3′′), 3.92-2.66
(m, 12 H), 3.61 (dd, 1 H, H-6′), 3.09-3.08 [d,
6 H, N(CH3)2], 3.67-3.63
(m, 1 H, H-5), 2.09-2.07 (d, 6 H, 2 × NHCOCH3). ¹³C
NMR (75 MHz, D2O): δ = 174.03, 173.79,
160.61, 100.58, 99.92, 86.79, 85.01, 80.48, 76.90, 73.63, 72.59,
70.11, 68.95, 66.40, 64.18, 60.97, 60.84, 59.20, 53.01, 52.63, 51.42, 37.60,
37.41, 22.05. ESI-MS: m/z = 645.2 [M + Na]+.