The influence of protecting groups on lipase catalyzed transesterifications: Enzymatic resolution of racemic cis-1,3-cyclopentanediol derivatives

Biocatalytic Selective Modifications of Conventional Nucleosides, Carbocyclic Nucleosides, and C-Nucleosides

“…Kobe and co-workers 87 tives similar to (()-210 (different substituents from trityl moiety) in vinyl acetate was greatly influenced by the size of the protecting groups at the additional trans-4-hydroxymethyl function (Scheme 52). 92 The highest regio-and enantioselectivities were obtained using the diol substrate protected with the bulky triphenylmethyl group. Thus, the racemic diol (()-210 was easily resolved by enzymatic transesterification.…”

“…Using cis -1,3-Cyclopentanediol Derivatives. The enzyme-catalyzed acetylation of racemic derivatives similar to (±)- 210 (different substituents from trityl moiety) in vinyl acetate was greatly influenced by the size of the protecting groups at the additional trans -4-hydroxymethyl function (Scheme ) . The highest regio- and enantioselectivities were obtained using the diol substrate protected with the bulky triphenylmethyl group.…”

Synthesis and Conformational and Biological Aspects of Carbasugars

“…Moser and co-workers 184 developed a related enzymecatalyzed acetylation for the synthesis of a carbocyclic 2-deoxyribose derivative (Scheme 23). The trityl-protected precursor (()-274, readily available from cyclopentadiene via 1,4-addition of singlet oxygen, 185 hydroformylation, reduction, and tritylation, was subjected to enzymatic acyl transfer with Chromobacterium Viscosum lipase, to give 2-deoxy-R-D-ribocarbafuranose derivative 275, with high enantioselectivity.…”

Lipase-Supported Synthesis of Biologically Active Compounds

“…The enantioselectivity of this reaction strongly depends on the protecting group at the primary hydroxy group, indicating that the trityl residue is superior to other substituents. 72 The butyl and hexyl ester of the cyclopentyl amines 61a,b have been resolved by hydrolysis with CCL to furnish both enantiomers almost enantiomerically pure.73 Finally, kinetic resolution of complete nucleoside analogs has been demonstrated. Lipase P-supported resolution of the racemic cis analog 62 could be successfully carried out74,75 followed by conversion of both enantiomers into the corresponding guanosine derivatives 63 and ent-63.…”