316186-17-1Relevant articles and documents
Asymmetric synthesis of methyl 6-deoxy-3-O-methyl-α-l-mannopyranoside from a non-carbohydrate precursor
Du, Wenting,Hu, Yongzhou
, p. 725 - 729 (2007/10/03)
A novel method is reported for preparing methyl 6-deoxy-3-O-methyl-α- l-mannopyranoside (1) by asymmetric synthesis, using 2-acetylfuran (2), a non-chiral simple molecule, as the starting material and achieving high yields via (S)-1-(2-furyl)ethanol and (
Development of a novel environmentally friendly electrolytic system by using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent: Application for Anodic methoxylation of organic compounds
Tajima, Toshiki,Fuchigami, Toshio
, p. 6192 - 6196 (2007/10/03)
We have successfully developed a novel environmentally friendly electrolytic system using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent. It was found that solid-supported bases are electrochemically inactive at an electrode surface. It was also found that solid-supported bases dissociate methanol into methoxide anions and protons. Therefore, in the presence of solid-supported bases, it was clarified that methanol serves as both a solvent and a supporting electrolyte generated in situ. Anodic methoxylation of various compounds with solid-supported bases was carried out to provide the corresponding methoxylated products in good to excellent yields with a few exceptions. The methoxylated products and the solid-supported bases were easily separated by only filtration, and the desired pure methoxylated products were readily isolated simply by concentration of the filtrates. The separated and recovered solid-supported bases were recyclable for several times.
Electroorganic synthesis of 2,5-dialkoxydihydrofurans and pyridazines on solid phase using polymer beads as supports
Nad, Sukanya,Breinbauer, Rolf
, p. 3654 - 3665 (2007/10/03)
Electroorganic synthesis has defied application in Solid-Phase Organic Synthesis (SPOS) so far. Typically more than 99.9% of the substrate molecules immobilized on a polymeric support are buried in the interior of the bead, and therefore are unable to undergo direct contact with a heterogeneous reagent such as an electrode. This intrinsic impediment for an electrochemical reaction can be overcome by the use of a redox mediator which shuttles electrons from the electrode to the polymer bound substrate molecules. This approach of indirect electroorganic synthesis was successfully applied for the 2,5-dialkoxylation of furans on solid phase. The oxidation products can be hydrolyzed and through condensation with hydrazine hydrate substituted pyridazines are produced in 50-65% overall yield. Georg Thieme Verlag Stuttgart.
Electroorganic synthesis on the solid phase using polymer beads as supports
Nad, Sukanya,Breinbauer, Rolf
, p. 2297 - 2299 (2007/10/03)
Chemistry with currents: The application of an indirect electroorganic approach has enabled electroorganic reactions on solid phases to be performed for the first time using commercially available polystyrene beads (see picture, Med = redox catalyst). The 2,5-dimethoxylation of a variety of furans was undertaken. This strategy can be integrated into multistep solid-phase synthesis.
SYNTHESIS OF (L)-DAUNOSAMINE AND RELATED AMINO SUGARS
Sammes, Peter G.,Thetford, Dean
, p. 111 - 124 (2007/10/02)
1-(2-Furyl)ethanol (6) has been converted into methyl (+/-)-daunosaminide (1) and methyl (+/-)-ristosaminide (3) by use of an intramolecular cyclisation of a trichloroacetimidate group. (+/-)-Daunosamine (1) has been obtained more directly from the alcohol (10) by use of a modified Mitsunobu reaction; the scope of the latter reaction has been explored using cyclohex-2-en-1-ol as a model substrate.Asymmetric reduction of 2-acetylfuran (5) has given (S)-1-(2-furyl)ethanol (46) in good enantiomeric excess, thus providing a short route to the L-enantiomers of the amino sugars (1), (2), and (3) from a cheap, non-carbohydrate precursor.
Chemoenzymic Synthesis of Chiral Furan Derivatives: Useful Building Blocks for Optically Active Structures
Drueckhammer, Dale G.,Barbas, Carlos F.,Nozaki, Kenji,Wong, Chi-Huey,Wood, Cynthia Y.,Ciufolini, Marco A.
, p. 1607 - 1611 (2007/10/02)
Practical procedures have been developed for the enantioselective reduction of 2-acetylfuran (6a) and 2-(trifluoroacetyl)furan (6b) to the corresponding carbinols (S)-1 and 7b with 88-90percent ee using Thermoanaerobium brockii alcohol dehydrogenase coupled with an NADPH regeneration system.Kinetic resolution of racemic (S)-1 via lipase-catalyzed esterification, followed by cholesterol esterase or lipase-catalyzed hydrolysis of the ester gives (R)-1 with 94percent ee.Conversion of (S)-1 to the dihydropyranones 4 and 5 without racemization has been illustrated.Enantioselectivehydrolysis of N-protected furylglycine methyl esters catalyzed by papain gave the unreacted esters and and the free acids (S form) both in 45percent yield and 97percent ee.The resolved furylglycines are excellent substrates for the synthesis of optically active synthons for alkaloids.
