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3?-Acet-oxy-lup-20(29)-en-28-yl 1H-1,2,4-tri-azole-1-carboxyl-ate.

ABSTRACT: The title triterpene, C(35)H(53)N(3)O(4), is a C-28 carbamate derivative of 3?-acet-oxy-betulin prepared in a one-step reaction from the commercially available 1,1'-carbonyl-di(1,2,4-triazole) (CDT), crystallized from acetone/n-hexane. All rings are trans fused. The carbamate and acetate substituents are in axial and equatorial positions, respectively. A quantum chemical ab initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol-ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.

SUBMITTER: Santos RC

PROVIDER: S-EPMC3009070 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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3β-Acet-oxy-lup-20(29)-en-28-yl 1H-1,2,4-tri-azole-1-carboxyl-ate.

Santos R C RC Matos Beja A A Salvador J A R JA Paixão J A JA

Acta crystallographica. Section E, Structure reports online 20101031 Pt 11

The title triterpene, C(35)H(53)N(3)O(4), is a C-28 carbamate derivative of 3β-acet-oxy-betulin prepared in a one-step reaction from the commercially available 1,1'-carbonyl-di(1,2,4-triazole) (CDT), crystallized from acetone/n-hexane. All rings are trans fused. The carbamate and acetate substituents are in axial and equatorial positions, respectively. A quantum chemical ab initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond length ...[more]

PMID: 21589195

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