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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
- 1
Sakuda S.Isogai A.Matsumoto S.Suzuki A. J. Anibiot. 1987, 40: 296 - 2
Berecibar A.Grandjean C.Siriwardena A. Chem. Rev. 1999, 99: 779 -
3a
Tanaka K.Fujimoto Y.Tanaka S.Mori Y.Fukase K. In Glycoscience Part 5:Fraser-Reid B.Tatsuta K.Thiem J. Springer; Berlin/Heidelberg: 2008. p.1205 -
3b
Plante OJ.Palmacci ER.Seeberger PH. Science 2001, 291: 1523 - 4
Manabe S.Ito Y. Chem. Pharm. Bull. 2001, 49: 1234 - 5
Watanabe Y.Kiyosawa Y.Hyodo S.Hayashi M. Tetrahedron Lett. 2005, 46: 281 - 6
Jeanloz RW. J. Am. Chem. Soc. 1957, 79: 2591 - 7
DeNinno MP.Etienne JB.Duplantier KC. Tetrahedron Lett. 1995, 36: 669 - 8
Melean LG.Love KR.Seeberger PH. Carbohydr. Res. 2002, 337: 1893 - 9
Corey EJ.Venkateswarlu A. J. Am. Chem. Soc. 1972, 94: 6190 - 10
Rivero IA.Somanathan R.Hellberg LH. Synth. Commun. 1993, 23: 711 - 11
Griffith DA.Danishefsky SJ. J. Am. Chem. Soc. 1991, 113: 5863 - 12
Reichardt N.-C.Martin-Lomas M. Angew. Chem. Int. Ed. 2003, 42: 4674
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]+.