103795-16-0Relevant academic research and scientific papers
Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 165 - 190 (2007/10/03)
Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.
Cycloaddition Reactions of Carbohydrate Derivatives. Part V. A Hetero Diels-Alder Approach to Swainsonine Analogs
Herczegh, Pal,Kovacs, Imre,Szilagyi, Laszlo,Sztaricskai, Ferenc,Berecibar, Amaya,et al.
, p. 13671 - 13686 (2007/10/02)
Diastereoselective hetero Diels-Alder reactions of sugar derived azomethines 4a-4g have been used for the construction of chiral piperidones 6 and 7.Configuration of the major products was 6,1'-threo in every case.The enone system of 6 and 7 was reduced d
Construction of all O-alkoxy D-tetrose and D-pentose stereoisomers from 2,3-O-isopropylidene-D-glyceraldehyde using 2-(trimethylsilyl)thiazole as a formyl anion equivalent
Dondoni,Orduna,Merino
, p. 201 - 210 (2007/10/02)
All D-tetroses and D-pentoses having differentially protected hydroxy groups are synthesized by an iterative one-carbon chain-elongation cycle commencing with the addition of 2-(trimethylsilyl)thiazole to 2,3-O-isopropylidene-D-glyceraldehyde. One half of
Iterative, Stereoselective Homologation of Chiral Polyalkoxy Aldehydes Employing 2-(Trimethylsilyl)thiazole as a Formyl Anion Equivalent. The Thiazole Route to Higher Carbohydrates
Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
, p. 693 - 702 (2007/10/02)
A new approach to long-chain sugars is demonstrated by the stereoselective conversion of D-glyceraldehyde acetonide (2a), L-threose acetonide (2b), and dialdogalactopyranose diacetonide (2h) into higher homologues up to C9, C7, and C
Chiral building units from carbohydrates-XIII. Identification of the absolute configuration of endo-brevicomin from dendroctonus frontalis and synthesis of both enantiomers from d-ribose
Redlich, Hartmut,Bruns, Wilfried,Francke, Wittko,Schurig, Volker,Payne, Thomas L.,Vite, Jean Pierre
, p. 2029 - 2034 (2007/10/02)
The synthesis of both enantiomers of endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.l]octana (endo-brevicomin, 12 and 12a) starting froni D-ri-bose is described. Key interinediate is the open chain derivative 7, a chiral building unit easily available from ca
