115114-57-3Relevant academic research and scientific papers
Stereoselectivity in the Lewis acid mediated reduction of ketofuranoses
Van Rijssel, Erwin R.,Van Delft, Pieter,Van Marle, Daan V.,Bijvoets, Stefan M.,Lodder, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.,Codée, Jeroen D.C.
, p. 4553 - 4565 (2015/05/13)
The Lewis acid mediated reduction of ribose-, arabinose-, xylose-, and lyxose-derived methyl and phenyl ketofuranoses with triethylsilane as nucleophile was found to proceed with good to excellent stereoselectivity to provide the 1,2-cis addition products
D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine
Doboszewski, Bogdan
experimental part, p. 875 - 901 (2010/08/19)
2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).
Synthesis of C-glycofuranosides by the stereoselective reduction of hemiacetals
Calzada, Eguzkine,Clarke, Catherine A.,Roussin-Bouchard, Christine,Wightman, Richard H.
, p. 517 - 518 (2007/10/02)
Reaction of protected glycofuranolactones with organolithium reagents and reduction of the resultant hemiacetals with triethylsilane-boron trifluoride gives a stereocontrolled route to C-glycofuranosides, with hydride delivery occurring cis-to an adjacent
STEREOSELECTIVITY IN THE ELECTROPHILE-MEDIATED CYCLIZATION OF 2,3,5-TRI-O-BENZYL-1,2-DIDEOXY-D-arabino-HEX-1-ENITOL. A STEREOCONTROLLED SYNTHESIS OF 1-AMINO-2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-1-DEOXY-D-GLUCITOL
Freeman, Fillmore,Robarge, Kirk D.
, p. 1 - 12 (2007/10/02)
Cyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enitol (2) with mercuric acetate, mercuric trifluoroacetate, iodine, and N-bromosuccinimide gave preponderantly the allo isomer of the C-arabinofuranosyl structure. 1-Amino-2,5-anhydro-3,4,6-tr
