327622-76-4Relevant articles and documents
Simple, efficient chemoenzymatic synthesis of (s)-5-(tert-butyldimethylsilyloxy)-2-cyclohexenone and enantiomeric ketone intermediates of 19-nor-1α,25-dihydroxyvitamin D3
Kalkote, Uttam R.,Ghorpade, Sandeep R.,Chavan, Subhash P.,Ravindranathan
, p. 8277 - 8281 (2001)
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Multiselective enzymatic reactions for the synthesis of protected homochiral cis- and trans-1,3,5-cyclohexanetriols
Wirz, Beat,Iding, Hans,Hilpert, Hans
, p. 4171 - 4178 (2007/10/03)
For the synthesis of the potentially antipsoriatic vitamin D derivative 3 (Ro 65-2299) an efficient and multiselective enzymatic step had been developed in which the easily accessible trans-1,3,5-triacetoxy-cyclohexane 5 was selectively monohydrolyzed in the presence of the cis-isomer 8 to give (1R,3R)-1,3-diacetoxy-5-hydroxy-cyclohexane 6 in high enantiomeric excess (>99%) and yield (84%). Furthermore, for the synthesis of the enantiomer of 3, a simple and efficient enzymatic procedure for the asymmetric acetylation of cis-1,5-dihydroxy-3-(tert-butyldimethylsilanoxy)-cyclohexane 10 in an anhydrous organic solvent providing (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanoxy)-cyclohexane 11 in >99% ee and quantitative yield is described. Copyright (C) 2000 Elsevier Science Ltd.