69349-72-0Relevant academic research and scientific papers
Experimental observations on the reductive cleavage of endo and exo 3,4-O-benzylidene fucopyranoside derivatives
Studzian, Maciej,Pérez, María-Elena,Arias-Pérez, María-Selma
, (2021)
Reductive cleavage of methyl 3,4-O-benzylidene-α-L-fucopyranosides with BH3·THF-TfOH and NaCNBH3-TfOH systems resulted in enhanced reaction rates and selectivity compared to BH3·THF-Bu2BOTf. With this latter sys
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.
