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The reaction of the peracetate methyl esters of N-acetylneuraminic acid (Neu5Ac), 3-deoxy-d-glycero-d-galacto-2-nonulosonic acid (Kdn), and 3-deoxy-d-manno-2-octulosonic acid (Kdo) with trimethylsilyl trifluoromethanesulfonate
β Scribed by Gaik B. Kok; Brendan L. Mackey; Mark von Itzstein
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 445 KB
- Volume
- 289
- Category
- Article
- ISSN
- 0008-6215
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β¦ Synopsis
The reaction of the peracetate methyl esters of N-acetylneuraminic acid (Neu5Ac), 3-deoxyq~glycero-D-galacto-2-nonulosonic acid (Kdn), and 3-deoxy-D-manno-2-octulosonic acid (Kdo) with trimethylsilyl trifluoromethanesulfonate (CF3SO3SiMe 3) has been reinvestigated. We have found that the choice of solvent, reaction temperature, and reaction time dramatically influence the outcome of this reaction.
π SIMILAR VOLUMES
Treatment of methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-cr-D-manno-oct-2ulopyranosonic acid, or its methyl ester, with refluxing methanolic O.lM hydrogen chloride for 16 h gave 95% of methyl (methyl 3-deoxy-a-D-manno-act-2-ulopyranosid)onate. Acetylation of the methyl ester of 3-deoxy-D-manno-act-2ulo
The favoured conformations of a series of C-glycosyl derivatives of 4,5:7,8-di-O-isopropylidene-3deoxy-D-munno-2-octulosonic acid (Kdo) esters were analyzed by n.m.r. spectroscopy and in one instance by X-ray crystallography. The Kdo derivatives were found to adopt a skew-boat conformation (& + OS,)