88825-52-9

Upstream product

• 88825-55-2 2,2-Dimethyl-propionic acid (2S,3aR,4R,6S,7S,7aR)-4-methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 88825-56-3 2,2-Dimethyl-propionic acid (2R,3aR,4R,6S,7S,7aR)-4-methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 
• 65529-48-8 methyl endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 

Relevant academic research and scientific papers

Regioselective Ring Opening of Selected Benzylidene Acetals. A Photochemically Initiated Reaction for Partial Deprotection of Carbohydrates

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.