- Synthesis of the polyketomycin disaccharide
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The disaccharide portion of the anthracycline antibiotic polyketomycin consists of the trideoxy sugar D-amicetose attached to the methyl-branched sugar L-axenose. The polyketomycin disaccharide was synthesized from methyl 2,3,6-trideoxy-α-D-erythro-hexopyranoside (methyl α-D-amicetoside) and phenyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-1-thio-α,β-L-xylo- hexopyranoside. The key coupling step was carried out by N-bromosuccinimide activation of the thioglycoside and gave the desired α (1→4) linked disaccharide exclusively in 71% yield, which was debenzylated by sodium and liquid ammonia.
- Micalizzi, Douglas S.,Dougherty, J. Patrick,Noecker, Lincoln A.,Smith, Garry R.,Giuliano, Robert M.
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p. 3183 - 3188
(2007/10/03)
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- Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues
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Starting with methyl 4,6-O-benzylidene-α-D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in
- Hoefner, Georg,Streicher, Benedikt,Wnsch, Bernhard
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p. 284 - 290
(2007/10/03)
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- Molecular recognition XI. The synthesis of extensively deoxygenated derivatives of the H-type 2 human blood group determinant and their binding by an anti-H-type 2 monoclonal antibody and the lectin 1 of Ulex europaeus
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The relative potencies of a wide variety of deoxygenated derivatives of the methyl glycoside of α-L-Fuc-(1->2)-β-D-Gal-(1->4)-β-D-GlcNAc (the H-type 2 human blood related trisaccharide) for the inhibition of the binding of an artificial H-type 2 antigen b
- Spohr, Ulrike,Paszkiewicz-Hnatiw, Eugenia,Morishima, Naohiko,Lemieux, Raymond U.
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p. 254 - 271
(2007/10/02)
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