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Synthesis and structural study of 5-nitro-6-(penta- O -acetylpentitol-1-yl)norbornenes

Identifieur interne : 003697 ( Main/Exploration ); précédent : 003696; suivant : 003698

Synthesis and structural study of 5-nitro-6-(penta- O -acetylpentitol-1-yl)norbornenes

Auteurs : E. Roman Galan [États-Unis] ; Derek J. Hodgson [États-Unis] ; Yoshinobu Yokomori [États-Unis] ; Ernest L. Eliel [États-Unis] ; M. Bueno Martinez [États-Unis] ; Juan A. Serrano Blazquez [Espagne]

Source :

Carbohydrate Research [ 0008-6215 ] ; 1987.

RBID : ISTEX:382096BF25780DBA80DE5E268A84853A77A2ED0F

Abstract

Uncatalyzed reaction between cyclopentadiene and (E)-3,4,5,6,7-pentaacetoxy-1-nitrohept-1-enes having the d-manno, d-galacto, and d-gluco configurations at C-3—C-7 led, in each case, to the four stereoisomeric 5-nitro-6-(1,2,3,4,5-penta-O-acetylpentitol-1-yl)bicyclo[2.2.1]hept-2-enes. Face selectivity is discussed in terms of the sugar-chain configuration. The structures assigned the adducts are based on their n.m.r. spectra, and, in the case of the d-manno compounds, on X-ray data. Also described are the 13C-n.m.r. spectra of the starting nitroalkenes. The crystal structures of (5S,6S)1,2,3,4,5-penta-O-acetyl-1-C-(5-exo-nitrobicyclo[2.2.1]hept-2-en-6-endo-yl-d-manno-pentitol (3a) and (5S,6S)1,2,3,4,5-penta-O-acetyl-1-C-(5-endo-nitrobicyclo[2.2.1]hept-2-en-6-exo-yl-d-manno-pentitol (5a) were determined from three-dimensional, X-ray data. Crystals of 3a are monoclinic, space group P21, with two molecules in a cell of dimensions a = 9.054(3), b = 15.580(11), c = 10.138(4) Å, β = 116.27(3)°. The structure was refined to an R-factor of 0.050 on the basis of 1485 observations. Crystals of 5a are triclinic, space group P1, with one molecule in a cell of dimensions a = 8.680(4), b = 9.760(4), c = 8.695(7) Å, α = 98.69(5), β = 103.13(5), γ = 112.09(3)°. The structure was refined to an R-factor of 0.074 based on 970 observations.

Url:

https://api.istex.fr/document/382096BF25780DBA80DE5E268A84853A77A2ED0F/fulltext/pdf

DOI: 10.1016/0008-6215(88)80083-1

Affiliations:

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Le document en format XML

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<front><div type="abstract" xml:lang="en">Uncatalyzed reaction between cyclopentadiene and (E)-3,4,5,6,7-pentaacetoxy-1-nitrohept-1-enes having the d-manno, d-galacto, and d-gluco configurations at C-3—C-7 led, in each case, to the four stereoisomeric 5-nitro-6-(1,2,3,4,5-penta-O-acetylpentitol-1-yl)bicyclo[2.2.1]hept-2-enes. Face selectivity is discussed in terms of the sugar-chain configuration. The structures assigned the adducts are based on their n.m.r. spectra, and, in the case of the d-manno compounds, on X-ray data. Also described are the 13C-n.m.r. spectra of the starting nitroalkenes. The crystal structures of (5S,6S)1,2,3,4,5-penta-O-acetyl-1-C-(5-exo-nitrobicyclo[2.2.1]hept-2-en-6-endo-yl-d-manno-pentitol (3a) and (5S,6S)1,2,3,4,5-penta-O-acetyl-1-C-(5-endo-nitrobicyclo[2.2.1]hept-2-en-6-exo-yl-d-manno-pentitol (5a) were determined from three-dimensional, X-ray data. Crystals of 3a are monoclinic, space group P21, with two molecules in a cell of dimensions a = 9.054(3), b = 15.580(11), c = 10.138(4) Å, β = 116.27(3)°. The structure was refined to an R-factor of 0.050 on the basis of 1485 observations. Crystals of 5a are triclinic, space group P1, with one molecule in a cell of dimensions a = 8.680(4), b = 9.760(4), c = 8.695(7) Å, α = 98.69(5), β = 103.13(5), γ = 112.09(3)°. The structure was refined to an R-factor of 0.074 based on 970 observations.</div>
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Synthesis and structural study of 5-nitro-6-(penta- O -acetylpentitol-1-yl)norbornenes

Synthesis and structural study of 5-nitro-6-(penta- O -acetylpentitol-1-yl)norbornenes

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Abstract

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