65529-46-6Relevant academic research and scientific papers
A new method for the deprotection of benzyl ethers or the selective protection of alcohols
Madsen, Jacob,Viuf, Christel,Bols, Mikael
, p. 1140 - 1146 (2007/10/03)
A new selective method for the deprotection of benzyl ethers situated next to alcohols in the α, β, or γ position is presented which uses either NIS or DIB/I2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is b
Regioselective Ring Opening of Selected Benzylidene Acetals. A Photochemically Initiated Reaction for Partial Deprotection of Carbohydrates
Binkley, Roger W.,Goewey, Gayle S.,Johnston, James C.
, p. 992 - 996 (2007/10/02)
A new method is described for regioselective partial deprotection of carbohydrates protected as benzylidene acetals.This deprotection was accomplished for each of the six methyl pyranosides (4,5, and 18-21) studied by irradiation of the protected sugar and N-bromsuccinimide (NBS) in the presence of water.Under these conditions the benzylidene (1,3-dioxolane) ring in each compound opened to give a methyl pyranoside with an axial benzoyloxy group and an equatorial hydroxy group.For example, irradiation of methyl 3,4-O-benzylidene (R or S)-6-deoxy-2-O-(2,2-dimethylpropanoyl)-α-L-galactopyranoside (18 or 19) with NBS, barium carbonate, and water resulted in the formation of methyl 4-O-benzoyl-6-deoxy-2-O-(2,2-dimethylpropanoyl)-α-L-galactopyranoside (22) in 72percent yield.In a similar manner compounds 4 and 5 gave 10 and compounds 20 and 21 produced 23.The advantages of the deprotection process are described.
