Synlett 2010(10): 1554-1556  
DOI: 10.1055/s-0029-1219932
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Synthesis of Allosamidin

Gang Liang Huang*, Yue Peng Dai
College of Chemistry, Chongqing Normal University, Chongqing 400047, P. R. of China
e-Mail: huangsome@hotmail.com;
Further Information

Publication History

Received 23 March 2010
Publication Date:
10 May 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.

    References and Notes

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13

Allosamidin 1
IR (KBr): 3500, 3365, 1652, 1550, 1060 cm. 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]+.