Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,-17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta-[a]phenanthren-17-yl]-N-methoxy-N-methylpropanamide (Fernholz Weinreb amide)

Elvar Ørn Viktorsson, Ove Alexander Høgmoen Åstrand, Rasha Sabah Haseeb, Carl Henrik Görbitz, Pal Rongved*, W. T A Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

The literature compound 3β-hydroxy-bisnor-5-cholenic aldehyde is an important intermediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important intermediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3β-hydroxy-bisnor-5-cholenic acid. The title amide crystallized with two molecules in the asymmetric unit, linked into helices by O - H⋯O hydrogen bonds involving the hydroxy and carbonyl groups.

Original languageEnglish
Pages (from-to)275-277
Number of pages3
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number3
DOIs
Publication statusPublished - 1 Mar 2015

Fingerprint

Aldehydes
aldehydes
Amides
amides
Crystal structure
crystal structure
liver
Liver
helices
Modulators
modulators
Hydrogen bonds
hydrogen bonds
acids
Molecules
Acids
synthesis
molecules
oxysterol binding protein
Cytoplasmic and Nuclear Receptors

Keywords

  • Crystal structure
  • Liver X receptor
  • Obesity
  • Steroid

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,-17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta-[a]phenanthren-17-yl]-N-methoxy-N-methylpropanamide (Fernholz Weinreb amide). / Viktorsson, Elvar Ørn; Åstrand, Ove Alexander Høgmoen; Haseeb, Rasha Sabah; Görbitz, Carl Henrik; Rongved, Pal; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 3, 01.03.2015, p. 275-277.

Research output: Contribution to journalArticle

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AU - Åstrand, Ove Alexander Høgmoen

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