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| Titel: |
Studies of the Synthesis of Rubranitrose and Crystal Structure of Methyl 2,3,6-Trideoxy-3-C-Methyl-3-Nitro-α-D-Ribo-Hexopyranoside |
| Auteur: |
Ye, Hong Noecker, Lincoln Boyko, Walter J. Giuliano, Robert M. Yap, Glenn P. A. Rheingold, Arnold L. |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 16 (1997) nr. 3 pagina's 373-383 |
| Jaar: |
1997-03-01 |
| Inhoud: |
The branched-chain nitro sugar methyl 2,3,6-trideoxy-3-C-methyl-3-nitro-α-D-ribo-hexopyranoside 4 was investigated as a precursor to D-rubranitrose, a nitro sugar found in the antibiotic rubradirin. X-ray cyrstallographic analysis of 4 shows that the pyranose ring adopts the 4C1 conformation with the methoxy group at C-1 and the nitro group at C-3 in a 1,3-diaxial relationship. There is an intermolecular hydrogen bond involving a nitro group oxygen of one monosaccharide residue and the C-4 hydroxyl group of the adjacent residue in the crystal lattice. This interaction results in a helical crystal packing. A series of nucleophilic displacement reactions was carried out on the triflate derivative of 4 in an attempt to introduce an axial carbon-oxygen bond at C-4 required for rubranitrose. Displacements with acetate and propionate gave as products the monosaccharide esters with the desired D-xylo configuration. |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 149 van 252 gevonden artikelen
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