Solid-Phase Synthesis of Allosamidin

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.

allosamidin - solid-phase synthesis - trichloroacetim­idate donors - Wang resin - glycosylation reactions

References and Notes

<A NAME="RS01310ST-1">1</A> Sakuda S. Isogai A. Matsumoto S. Suzuki A. J. Anibiot.  1987,  40:  296 

<A NAME="RS01310ST-2">2</A> Berecibar A. Grandjean C. Siriwardena A. Chem. Rev.  1999,  99:  779 

<A NAME="RS01310ST-3A">3a</A> 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 

<A NAME="RS01310ST-3B">3b</A> Plante OJ. Palmacci ER. Seeberger PH. Science  2001,  291:  1523 

<A NAME="RS01310ST-4">4</A> Manabe S. Ito Y. Chem. Pharm. Bull.  2001,  49:  1234 

<A NAME="RS01310ST-5">5</A> Watanabe Y. Kiyosawa Y. Hyodo S. Hayashi M. Tetrahedron Lett.  2005,  46:  281 

<A NAME="RS01310ST-6">6</A> Jeanloz RW. J. Am. Chem. Soc.  1957,  79:  2591 

<A NAME="RS01310ST-7">7</A> DeNinno MP. Etienne JB. Duplantier KC. Tetrahedron Lett.  1995,  36:  669 

<A NAME="RS01310ST-8">8</A> Melean LG. Love KR. Seeberger PH. Carbohydr. Res.  2002,  337:  1893 

<A NAME="RS01310ST-9">9</A> Corey EJ. Venkateswarlu A. J. Am. Chem. Soc.  1972,  94:  6190 

<A NAME="RS01310ST-10">10</A> Rivero IA. Somanathan R. Hellberg LH. Synth. Commun.  1993,  23:  711 

<A NAME="RS01310ST-11">11</A> Griffith DA. Danishefsky SJ. J. Am. Chem. Soc.  1991,  113:  5863 

<A NAME="RS01310ST-12">12</A> Reichardt N.-C. Martin-Lomas M. Angew. Chem. Int. Ed.  2003,  42:  4674 

<A NAME="RS01310ST-13">13</A>

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]⁺.