14086-10-3Relevant academic research and scientific papers
Oxidation-hydroxymethylation-reduction: A one-pot three-step biocatalytic synthesis of optically active α-aryl vicinal diols
Shanmuganathan, Saravanakumar,Natalia, Dessy,Greiner, Lasse,Dominguez De Maria, Pablo
scheme or table, p. 94 - 97 (2012/03/26)
A one-pot multi-step approach comprising enzymatic oxidation- hydroxymethylation-reduction enables the synthesis of optically active α-aryl vicinal diols with high yields and enantioselectivities. Formaldehyde required for the hydroxymethylation step is enzymatically produced in situ using less hazardous methanol as substrate.
Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
Kallinen, Annukka,Tois, Jan,Sjoeholm, Rainer,Franzen, Robert
experimental part, p. 2367 - 2371 (2010/12/25)
Stereoselective synthesis of (5R,6R)- and (5S,6S)-5-benzylamino-6-(tert- butyldimethylsilanyloxymethyl)-5,6-dihydropyran-2-ones starting from d-glucal and furanaldehyde, respectively, is described. The synthesis relies on a Sharpless asymmetric dihydroxylation, an Achmatowicz reaction, and a stereoselective Pd-catalyzed allylic amination as the key steps.
Total synthesis and anti-leishmanial activity of R-(-)-argentilactone
Saeed, Muhammad,Ilg, Thomas,Schick, Miriam,Abbas, Muhammad,Voelter, Wolfgang
, p. 7401 - 7403 (2007/10/03)
Starting from the commercially available D-glucal (2), the naturally occurring α,β-unsaturated δ-lactone argentilactone (1a) has been synthesized. The important step is the configuration inversion at C-6 by the Mitsunobu reaction following the sugar-non-sugar-sugar strategy. The synthetic argentilactone has been tested against Leishmania mexicana for bioactivity.
Syntheses of four D- and L-hoxoses via diastereoselective and enantioselective dihydroxylation reactions
Harris, Joel M.,Keraenen, Mark D.,Nguyen, Hang,Young, Victor G.,O'Doherty, George A.
, p. 17 - 36 (2007/10/03)
An expeditious approach to various protected hexoses has been developed by the use of the Sharpless catalytic asymmetric dihydroxylation reaction. Applying the Sharpless catalytic asymmetric dihydroxylation reaction on vinylfuran, diols with high enentioexcess are produced. The resulting diols can be stereoselectively transformed into either protected D- or L-mannose in five steps and approximately 39% yield from furfural. Similarly, both D- and L-talose and gulose have been synthesized in 19% overall yields, respectively. Using a modified strategy, both protected D- and L-gulo- and allo-sugar-δ-lactones were synthesized in eight steps and ~-20% overall yield from furfural. (C) 2000 Elsevier Science Ltd.
A SIMPLE PROCEDURE FOR THE PREPARATION OF L-HEXOSES
Hauser, Frank M.,Ellenberger, Suzanne R.,Ellenberger, William P.
, p. 4939 - 4942 (2007/10/02)
A brief route for preparation of the L-hexenulose 4 from D-glucal 1 via furan intermediates 2 and 3 is described.
