108211-36-5Relevant articles and documents
Chirale Synthesebausteine durch Kolbe-Elektrolyse enantiomerenreiner β-Hydroxy-carbonsaeurederivate, (R)- und (S)-Methyl- sowie (R)-Trifluormethyl-γ-butyrolactone und δ-valerolactone
Seebach, Dieter,Renaud, Philippe
, p. 2342 - 2349 (1985)
The coupling of chiral, non-racemic R* groups by Kolbe electrolysis of carboxylic acids R*COOH is used to prepare compounds with a 1,4- and 1,5-distance of the functional groups.The suitably protected β-hydroxycarboxylic acids (R)- or (S)-3-hydroxybutyric acid, (R)-4,4,4-trifluoro-3-hydroxybutyric acid (as acetates; see 1-6), and (S)-malic acid (as (2S,5S)-2-(tert-butyl)-5-oxo-1,3-dioxolan-4-acetic acid, see 7) are decarboxylatively dimerized or "codimerized" with 2-methylpropanoic acid, with 4-(formylamino)butyric acid, and with monomethyl malonate and succinate.The products formed are derivatives of (R,R)-1,1,1,6,6,6-hexafluoro-2,5-hexanediol (see 8), of (R)-5,5,5-trifluoro-4-hydroxypentanoic acid (see 9, 10), of (R)- and (S)-5-hydroxyhexanoic acid (see 11) and its trifluoro analogue (see 12, 13), of (S)-2-hydroxy- and (S,S)-2,5-dihydroxyadipic acid (see 23, 20), of (S)-2-hydroxy-4-methylpentanoic acid ("OH-leucine", see 21), and of (S)-2-hydroxy-6-aminohexanoic acid ("OH-lysine", see 22).Some of these products are further converted to CH3- or CF3-substituted γ- and δ- lactones of (R)- or (S)-confuguration (14, 16-19), or to an enantiomerically pure derivative of (R)-1-hydroxy-2-oxocyclopentane-1-carboxylic acid (see 24).Possible uses of these new chiral building blocks for the synthesis of natural products and their CF3 analogues (brefeldin, sulcatol, zearalenone) are discussed.The olfactory properties of (R)- and (S)-δ-caprolactone (18) are compared with those of (R)-6,6,6-trifluoro-δ-caprolactone (19).
SERINE/THREONINE KINASE INHIBITORS
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Paragraph 00362, (2015/07/16)
Compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such diseases, or associated pathological conditions are disclosed.
On the structure of PHB (=Poly[(R)-3-hydroxybutanoic acid]) in phospholipid bilayers: Preparation of trifluoromethyl-labeled oligo[(R)-3-hydroxybutanoic acid] derivatives
Rueping, Magnus,Albert, Matthias,Seebach, Dieter
, p. 2473 - 2486 (2007/10/03)
Oligomers of (R)-3-hydroxybutanoate (OHB) have previously been shown to transport cations through lipid bilayers. The ion-transport activity has been attributed to the formation of hydrophobic aggregates or pores, which have been identified by fluorescenc
