114877-89-3Relevant academic research and scientific papers
Redox glycosidation: the use of Nozaki-Takai methylenylation in a highly stereoselective synthesis of sucrose
Barrett, Anthony G. M.,Melcher, Laura M.,Bezuidenhoudt, Barend C. B.
, p. 259 - 272 (2007/10/02)
Sequential reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (7) with butyllithium and 2-thio-3-nitropyridine (6) at -78 deg C gave 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 2,3,5-tri-O-benzyl-4-O-(tert-butyldiphenylsilyl)-D-arabinonate (8: 71percent, α:β > 50:1).Ester carbonyl methylenylation, desilylation, and iodoetherification in the presence of silica gave 3,4,6-tri-O-benzyl-1-deoxy-1-iodo-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-fructofuranoside (15: 44percent, α:β > 50:1).This neopentylic iodide 15 was converted into sucrose (1: 80percent) by free-radical substitution using TEMPO (24) followed by sodium-ammonia reduction, acetylation and Zemplen methanolysis.
Application of (Chloromethyl)aluminum 2-(2-Propenyl)anilide in the Conversion of γ- and δ-Lactones into Protected Hydroxy Acids
Barrett, Anthony G. M.,Bezuidenhoudt, Barend C. B.,Dhanak, Dashyant,Gasiecki, Alan F.,Howell, Amy R.,et al.
, p. 3321 - 3324 (2007/10/02)
A series of γ- and δ-lactones including several aldonolactones were reacted with (chloromethyl)aluminum 2-(2-propenyl)anilide to produce the corresponding hydroxy amides.Protection using methyl chloride, (2-methoxyethoxy)methyl chl
CHLOROMETHYLALUMINUM 2-(2-PROPENYL)ANILIDE - A CONVENIENT REAGENT FOR THE CONVERSION OF LACTONES INTO PROTECTED HYDROXY ACIDS
Barrett, Anthony G.M.,Dhanak, Dashyant
, p. 3327 - 3330 (2007/10/02)
The title reagent reacts with γ and δ lactones to provide hydroxy amides which can be easily converted into protected N-acyl indoles.Mild saponification provides indole and the protected hydroxy acid.
