Article ID Journal Published Year Pages File Type
1350049 Tetrahedron: Asymmetry 2005 8 Pages PDF
Abstract

Five chiral macrocyclic bisamides derived from d-mannitol and l-threitol, possessing C2 symmetry, were obtained by a macrocyclization reaction under two different conditions (MeOH, 12 kbar, rt or MeONa/MeOH, 1 bar, rt). Their applications for alkali metal binding processes are studied using ESI-MS technique.

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2,3-Bis-O-(2-aminoethyl)-1,4-di-O-benzyl-l-threitolC22H32N2O4[α]D21 = +8.9 (c 2.05; CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: 2S,3S

(7S,8S)-7,8-Bis(benzyloxymethyl)-6,9-dioxa-3,12,18-triaza-bicyclo[12.3.1]octadeca-1(17),14(18),15-triene-2,13-dioneC29H33N3O6[α]D24 = −28.8 (c 2.1; CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: 7S,8S

(10R,11R)-10,11-Di-[(4R)-2,2-dimethyl-1,3-dioxalane-4-yl]-3,9,12,18-tetraoxa-6,15,24-triaza- bicyclo[18.3.1]tetracosa-1(23),20(24),21-triene-5,16-dioneC27H41N3O10[α]D20 = +15.8 (c 2.1; CHCl3)Source of chirality: d-mannitolAbsolute configuration: 10R,11R,4′R,4″R

(13R,14R)-13,14-Bis(2,2-dimethyl-[1,3]dioxalan-4-yl)-3,9,12,15,18,24-hexaoxa-6,21,30-triaza-bicyclo[24.3.1]triaconta-1(29),26(30),27-triene-5,22-dioneC31H49N3O12[α]D20 = +10.6 (c 1.0, CHCl3)Source of chirality: d-mannitolAbsolute configuration: 13R,14R,4′R,4″R

(10S,11S)-10,11-Bis(benzyloxymethyl)-3,9,12,18-tetraoxa-6,15,24-triaza-bicyclo[18.3.1]tetracosa-1(23),20(24),21-triene-5,16-dioneC33H41N3O8[α]D24 = +2.2 (c 2.2; CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: 10S,11S

(13S,14S)-13,14-Bis-benzyl-oxymethyl-3,9,12,15,18,24-hexaoxa-6,12,30-triaza-bicyclo[24.3.1]triaconta-1(29),26(30),27-triene-5,22-dioneC37H49N3O10[α]D20 = +14.6(c 1.0, CHCl3)Source of chirality: l-tartaric acidAbsolute configuration: 13S,14S

Related Topics
Physical Sciences and Engineering Chemistry Inorganic Chemistry
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