326586-22-5Relevant academic research and scientific papers
Gold(i)-catalyzed C-glycosylation of glycosyl: Ortho -alkynylbenzoates: The role of the moisture sequestered by molecular sieves
Chen, Xiaoping,Wang, Qiaoling,Yu, Biao
, p. 12183 - 12186 (2016)
C-Glycosylation of glycosyl ortho-hexynylbenzoates with allyltrimethylsilane or silyl enol ethers could proceed smoothly under the catalysis of Ph3PAuNTf2 to provide the corresponding C-glycosides in high yields and stereoselectivity, wherein the moisture sequestered by the molecular sieves was disclosed to play a critical role in the gold(i)-catalytic cycle.
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).
