Synthesis of methyl 3,6-dideoxy-3-C-methoxycarbonyl-3-C-nitrohexopyranosides: crystal structure of methyl 3,6-dideoxy-3-C-methoxycarbonyl-3-C-nitro-α- l-galacto-hexopyranoside
✍ Scribed by Francisca Cabrera Escribano; Rosario Fernández-Fernández; Antonio Gómez-Sánchez; Isidro Hermosín Gutiérrez; Amparo López-Castro; María Dolores Estrada
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 537 KB
- Volume
- 199
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
✦ Synopsis
Methyl 3,6-dideoxy-3-C-methoxycarbonyl-3-C-nitro-a-L-ga~ac~o-hexopyranoside (3) has been synthesised by periodate oxidation of methyl a-L-rhamnopyranoside followed by condensation with methyl nitroacetate, and its structure has been established on the basis of its analytical and spectral data, and by an X-ray diffraction study. Crystals of 3 are orthorhombic, space group P2,2,2,, with a = 10.009(3), b = 15.3610(3), c = 7.986(3) A, and Z = 4. Molecular-packing analysis in the atom-atom approach yields an equilibrium configuration in good agreement with the experimental findings,
📜 SIMILAR VOLUMES
Studies of the Synthesis of Rubranitrose and Crystal Structure of Methyl 2,3,6-Trideoxy-3-C-methyl-3-nitro-α-D-ribo-hexopyranoside. -The title hexopyranoside (II) is investigated as a precursor to D-rubranitrose, a nitro sugar found in the antibiotic rubradirin. -(YE, H.; NOECKER,
ABSTRACf Previously unknown methyl 2,3-diacetamido-2,3-dideoxy-a-D-hexopyranosides having the gulo, allo, galacto, ido, and altro configurations, as well as 2,3-diacetamido-2,3-dideoxy-D-galactose, have been synthesised. 13C-N.m.r. data for all eight methyl 2,3-diacetamido-2,3-dideoxy-cu-D-hexopyran
The oxirane ring of 1,6:3,4-dianhydro-beta-D-talopyranose reacted at C-4 with methylamine, and the product, further processed gave a 3-deoxy-C-3-methylene derivative. Iodonium ion-induced cyclisation led to an iodooxazolidinone, and deiodination, followed by hydrolysis and N-acetylation, to the titl
L-Decilonitrose2 (1, 2,3,6-trideoxy-3-C-methyl-3-nitro-L-ribo-hexose) is the latest methyl-branched nitro sugar to be found as an antibiotic component. Other members of this novel group of sugars are L-evernitrose3 (2, from the evernino-micins4), D-rubranitrose5 (3, from rubradirin6), and D-kijanos