98815-79-3Relevant academic research and scientific papers
THE UNEXPECTED INTRAMOLECULAR C-ARYLATION OF 2-O-BENZYLATED CYCLIC SUGAR DERIVATIVES: A USEFUL 1,2-CIS-C-GLYCOSYLATION REACTION
Martin, O. R.
, p. 2055 - 2058 (1985)
Upon treatment with tin(IV) chloride, perbenzylated glycofuranosyl acetates such as 3 or 6 undergo an unusual, intramolecular α-C-arylation resulting from the internal Friedel-Crafts alkylation of the 2-O-benzyl substituent.
STRUCTURAL ELUCIDATION AND A NOVEL REDUCTIVE CLEAVAGE OF RIBOFURANOSYL RING C-1 - O BOND OF THE INTRAMOLECULAR C-ARYLATION PRODUCT OF TRI-O-BENZYL-β-D-RIBOFURANOSYL FLUORIDE
Araki, Younosuke,Mokubo, Eiji,Kobayashi, Naoki,Nagasawa, Jun'ichi,Ishido, Yoshiharu
, p. 1115 - 1118 (2007/10/02)
Treatment of 2,3,5-tri-o-benzyl-β-D-ribofuranosyl fluoride (1) with BF3*OEt2 in CH2Cl2 gave the intramolecular C-arylation product (2) formed from the reaction with the 2-O-benzyl group in a 83percent yield.Catalytic transfer hydrogenolysis of 2 using HCO
Intramolecular C-arylation of 2,3,5-tri-O-benzyl- and 2,3,5-tri-O-(3-methylbenzyl)-pentofuranose derivatives.
Martin
, p. 211 - 222 (2007/10/02)
Upon treatment with tin(IV) chloride, 1-O-acetyl-2,3,5-tri-O-benzyl- and 1-O-acetyl-2,3,5-tri-O-(3-methylbenzyl)pentofuranose (D-ribo, L-arabino) undergo intramolecular Friedel-Crafts alkylation of the aromatic substituent at O-2 to give unusual internal
HIGHLY STEREOSELECTIVE C-α-D-RIBOFURANOSYLATION. REACTIONS OF D-RIBOFURANOSYL FLUORIDE DERIVATIVES WITH ENOL TRIMETHYLSILYL ETHERS AND ALLYLTRIMETHYLSILANE
Araki, Younosuke,Kobayashi, Naoki,Ishido, Yoshiharu,Nagasawa, Jun'ichi
, p. 125 - 140 (2007/10/02)
2,3,5-Tri-O-methyl-D-ribofuranosyl fluoride (6), 2,3-di-O-benzyl-5-O-methyl-D-ribofuranosyl fluoride (7), and 5-O-benzyl-2,3-di-O-methyl-D-ribo-furanosyl fluoride (8) were obtained in 57 (6α, 15; and 6β, 42), 87 (7α, 22; and 7β, 65) and 85.5 (8α, 35.5; an
