TY - JOUR
T1 - Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides
AU - Skaanderup, Philip Robert
AU - Poulsen, Carina Storm
AU - Hyldtoft, Lene
AU - Jørgensen, Malene R.
AU - Madsen, Robert
PY - 2002
Y1 - 2002
N2 - Two methods are described for the regioselective displacement of the primary hydroxy group in methyl glycosides with iodide. The first method is a modification of a literature procedure employing triphenylphosphine and iodine, where purification has been carried out on a reverse phase column in order to efficiently separate the desired iodoglycosides from triphenylphosphine oxide. The second method employs a new procedure using sulfonylation in pyridine with sterically hindered 2,4,6-trichloro- and 2,4,6-tribromobenzenesulfonyl chloride. The sulfonates thus formed are effective leaving groups and substitution with iodide can be carried out in a one-pot process. Protection of the iodoglycosides is also described either by benzylation with benzyl trichloroacetimidate or silylation with triethylsilyl chloride.
AB - Two methods are described for the regioselective displacement of the primary hydroxy group in methyl glycosides with iodide. The first method is a modification of a literature procedure employing triphenylphosphine and iodine, where purification has been carried out on a reverse phase column in order to efficiently separate the desired iodoglycosides from triphenylphosphine oxide. The second method employs a new procedure using sulfonylation in pyridine with sterically hindered 2,4,6-trichloro- and 2,4,6-tribromobenzenesulfonyl chloride. The sulfonates thus formed are effective leaving groups and substitution with iodide can be carried out in a one-pot process. Protection of the iodoglycosides is also described either by benzylation with benzyl trichloroacetimidate or silylation with triethylsilyl chloride.
M3 - Journal article
SN - 0039-7881
SP - 1721
EP - 1727
JO - SYNTHESIS-STUTTGART
JF - SYNTHESIS-STUTTGART
IS - 12
ER -