All-α-d-linked tetra- and penta-saccharide substructures of Trestatin A by block syntheses with triflic anhydride as promoter
作者： Hans Peter Wessel , Beatrice Mayer , Gerhard Englert
DOI: 10.1016/0008-6215(93)80028-D
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摘要: Abstract The perbenzylated maltosyl and maltotriosyl fluorides 6 16 were treated with 2,3,2′,3′,6′-penta- O -benzyl-4,6- -benzylidene-α,α-trehalose ( 7 ) using triflic anhydride as a promoter to give all-α- d -linked tetra- penta-saccharides which finally deblocked the free oligosaccharides 4- -α-maltosyl- 9 -α-maltotriosyl-α,α-trehaloses 18 . 1 H NMR spectra of some compounds fully analyzed by 1D TOCSY ROESY experiments.
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sci-hub.se 参考文章(16)
Sankaran Subramanian, Ad Bax, Generation of Pure Phase NMR Subspectra for Measurement of Homonuclear Coupling Constants Journal of Magnetic Resonance. ,vol. 71, pp. 325- 330 ,(1987) , 10.1016/0022-2364(87)90063-1
Ken'ichi Takeo, Tohru Imai, Synthesis of trisaccharide glycosides related to nigeran Carbohydrate Research. ,vol. 165, pp. 123- 128 ,(1987) , 10.1016/0008-6215(87)80086-1
Hans Peter Wessel, Comparison of catalysts in α-glucosylation reactions and identification of triflic anhydride as a new reactive promoter. Tetrahedron Letters. ,vol. 31, pp. 6863- 6866 ,(1990) , 10.1016/S0040-4039(00)97191-0
Hans Peter Wessel, Nicolas Ruiz, α-Glucosylation Reactions with 2,3,4,6-Tetra-O-Benzyl-β-D-Glucopyranosyl Fluoride and Triflic Anhydride as Promoter Journal of Carbohydrate Chemistry. ,vol. 10, pp. 901- 910 ,(1991) , 10.1080/07328309108543958
Yukio Takahashi, Tomoya Ogawa, Total synthesis of cyclomaltohexaose Carbohydrate Research. ,vol. 164, pp. 277- 296 ,(1987) , 10.1016/0008-6215(87)80136-2
Hans Peter Wessel, Gerhard Englert, Peter Stangier, α‐D‐Glycosyl‐Substituted α,α‐D‐Trehaloses with (1 → 4)‐Linkage: Syntheses and NMR Investigations Helvetica Chimica Acta. ,vol. 74, pp. 682- 696 ,(1991) , 10.1002/HLCA.19910740403
Matthias Kreuzer, Joachim Thiem, Aufbau von oligosacchariden mit glycosylfluoriden unter lewissäure-katalyse☆ Carbohydrate Research. ,vol. 149, pp. 347- 361 ,(1986) , 10.1016/S0008-6215(00)90057-0
Hans Peter Wessel, Markus Hosang, Thomas B. Tschopp, Bernd-Jürgen Weimann, Heparin, carboxyl-reduced sulfated heparin, and Trestatin A sulfate. Antiproliferative and anticoagulant activities Carbohydrate Research. ,vol. 204, pp. 131- 139 ,(1990) , 10.1016/0008-6215(90)84028-S
Ken'ichi Takeo, Kayoko Mine, Takashi Kuge, Synthesis of methyl α- and β-maltotriosides and aryl β-maltotriosides Carbohydrate Research. ,vol. 48, pp. 197- 208 ,(1976) , 10.1016/S0008-6215(00)83215-2
Tommy Iversen, David R. Bundle, Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens Carbohydrate Research. ,vol. 103, pp. 29- 40 ,(1982) , 10.1016/S0008-6215(82)80005-0