114418-32-5Relevant academic research and scientific papers
Chemoenzymatic approaches to SCH 56592, a new azole antifungal
Morgan, Brian,Stockwell, Brent R.,Dodds, David R.,Andrews, David R.,Sudhakar, Anantha R.,Nielsen, Christopher M.,Mergelsberg, Ingrid,Zumbach, Arne
, p. 1361 - 1370 (1997)
Chemoenzymatic approaches to the synthesis of two key chiral precursors of a new azole antifungal agent, SCH 56592, are described. In particular, the enzymatic diastereoselective acylation of 2-benzyloxy-3-pentanol (7) was developed to produce (2S,3R)-7 in >97% diastereomeric excess (de) from otherwise unusable mixtures of (25,3R)/(2S,3S)-7 (40-80% de). The selectivity and reactivity of commercially available Candida rugosa and Mucor miehei Upases are compared for the acylation of 7 and the hydrolysis of the corresponding butyrate 16a. Of the 17 C. rugosa enzyme preparations that were examined for acylation of 7, two purified enzyme preparations showed no reactivity, five enzymes showed high diastereoselectivity with preference for the (2S,3R)-isomer, and seven showed a slight preference for the (2S,3S) isomer.
A new type of complex reagent, R4Pb / TiCl4
Yamamoto, Yoshinori,Yamada, Jun-Ichi,Asano, Tetsuya
, p. 5587 - 5596 (2007/10/02)
Tetraalkllleads (R4Pb) reacted quite smoothly with aldehydes R'CHO in the presence of TiCl4 to produce the corresponding alcohols (RCHOHR′) in high to good yields. The reagent system, R4Pb/ TiCl4, exhibited high chemoselectivity; only aldehydes underwent the alkylation in the presence of ketones. Further, the new reagent exhibited high 1,2- and 1,3-asymmetric induction. The transfer order of alkyl groups in the reaction of aldehydes with mixed tetraalkylleads/TiCl4 was determined; Me>Et.i-Pr?n-Bu.
Diols obtained via chemo and regioselective ring opening of epoxy alcohols: A straightforward synthesis of 2S,3S-octandiol
Bonini, Carlo,Righi, Giuliana
, p. 1531 - 1538 (2007/10/02)
Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.
STEREOCONTROLLED ONE-POT CONVERSIONS OF α-ALKOXY ESTERS TO SYN- AND ANTI-1,2-DIOL DERIVATIVES
Burke, Steven D.,Deaton, David N.,Olsen, Robert J.,Armistead, David M.,Blough, Bruce E.
, p. 3905 - 3906 (2007/10/02)
Complementary one-pot methods for the sequential addition of carbon and hydride nucleophiles to α-alkoxy esters leading to syn or anti mono-protected vicinal glycol derivatives are described.
