Stereoselective reactions of 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexopyranosyl) uracil with some nucleophiles

Article abstract of DOI:10.1080/07328319608002131

Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranosyl)uracil (4b) gave the corresponding 2-(substituted-amino)-3-deoxy-3-nitro-β-D-glucopyranosides (6a-f and 6h). Reaction of 4b with N,N′-carbonyldiimidazole directly gave 6g. Compound 4b was converted into the 2-deoxy analogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino analogue (10). The crystal structure of 5′-amino-5′-deoxyadenosine (5′-Am.dA) p-toluenesulfonate has been determined by X-ray crystallographic methods. It belongs to the orthorhombic space group P2₁2₁2₁ with a=7.754(3)A, b=8.065(1)A and c=32.481(2)A. This nucleoside shows a syn conformation about the glycosyl bond and C2′-endo-C3′-exo puckering for the ribose sugar. The orientation of N5′ atom is gauche-trans about the exocyclic C4′-C5′ bond. The amino nitrogen N5′ forms a trifurcated hydrogen bond with N3, O9T and O4′ atoms. Adenine bases form A.A.A triplets through hydrogen bonding between N6, N7 and N1 atoms of symmetry related nucleoside molecules.

Full text of DOI:10.1080/07328319608002131

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Nucleosides and Nucleotides
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Stereoselective Reactions OF
1-(4,6-O-Benzylidene-2,3-
Didehydro-2,3-dideoxy-3-nitro-β-
D-hexopyranosyl)uracil with some
Nucleophiles
N. Ohta a , K. Minamoto a , Y. Yamamoto a , N. Koide a & R.
Sakoda b
a Department of Applied Chemistry, School of Engineering ,
Nagoya University , Furo-cho, Chikusa-ku, Nagoya, 464, Japan
b Synthesis Research Dept. , Central Research Institute Nissan
Chemical Industries, Ltd. , 722–1, Tsuboi-cho, Funabashi-shi,
Chiba, 274, Japan
Published online: 20 Aug 2006.
To cite this article: N. Ohta , K. Minamoto , Y. Yamamoto , N. Koide & R. Sakoda (1996)
Stereoselective Reactions OF 1-(4,6-O-Benzylidene-2,3-Didehydro-2,3-dideoxy-3-nitro-β-D-
hexopyranosyl)uracil with some Nucleophiles , Nucleosides and Nucleotides, 15:4, 833-855, DOI:
10.1080/07328319608002131
To link to this article: http://dx.doi.org/10.1080/07328319608002131
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