Design and synthesis of regioselective cleaving reagents for oligonucleotides.
Reaction of methyl 2,3-anhydro-alpha-D-ribofuranoside with allylmagnesium chloride selectively took place at the 2-C position to afford methyl 2-C-allyl-2-deoxy-alpha-D-arabinofuranoside. 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose reacted with allylic alcohols in the presence of BF3.OEt2 to give the corresponding allyl beta-D-ribofuranosides. The allyl group in these compounds were converted into a variety of functional groups which include bromoacetoxy, oxylanyl, tosyloxy, and azide.
Mori
S
S
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University, Tokyo, Japan.
Ohgo
Y
Y
Tanaka
H
H
Katoh
A
A
Kaji
H
H
Samejima
T
T
Mitsunobu
O
O
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000498:Allyl Compounds; D007202:Indicators and Reagents; D009841:Oligonucleotides; C084403:methyl 2-C-allyl-2-deoxyarabinofuranoside; C084404:allyl ribofuranoside; D012266:Ribose; D001089:Arabinose