115040-65-8Relevant academic research and scientific papers
A simple and efficient PdCl2 mediated conversion of γ,δ-olefinic alcohols into C-glycosides
Sharma,Subash Chander,Krishnudu,Krishna, Palakodety Radha
, p. 9051 - 9054 (1997)
An efficient and mild intramolecular oxidative nucleophilic cyclisation protocol has been developed for the conversion of γ, δ-olefinic alcohols into the hemiketals, which in turn on deoxygenation led to the very important C-glycoside class of compounds.
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).
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
