TY - JOUR
T1 - Novel carbohydrate-based mono- and bidentate oligosilyl ethers
AU - Flemming, Anke
AU - Mamat, Constantin
AU - Köckerling, Martin
AU - Krempner, Clemens
AU - Miethchen, Ralf
PY - 2006/8/17
Y1 - 2006/8/17
N2 - Regioselective one-pot O-silylation reactions of 1,2-O-isopropylidene- α-D-glucofuranose and 1,2-O-isopropylidene-β-D-fructopyranose using bulky oligosilyl groups are described. Some new silylating reagents (oligosilyl bistriflates), which were generated in situ from readily available phenylsilanes, resulted in 5,6-O-(glucofuranose) and 4,5-O-bridged (fructopyranose) carbohydrates with favoured seven- and eight-membered rings. In these cyclic oligosilyl diethers, three and four ring atoms, respectively, are Si atoms. It is noteworthy, that the seven-membered ring of 5,6-O-[2,4- bis(trimethylsilyl)-1,1,1,3,3,5,5,5-octamethylpentasilan-2,4-diyl]-1, 2-O-isopropylidene-α-D-glucofuranose was expanded to an eight-membered ring by regioselective insertion of aerial oxygen into one of the Si-Si bonds. X-ray analyses of some derivatives are presented.
AB - Regioselective one-pot O-silylation reactions of 1,2-O-isopropylidene- α-D-glucofuranose and 1,2-O-isopropylidene-β-D-fructopyranose using bulky oligosilyl groups are described. Some new silylating reagents (oligosilyl bistriflates), which were generated in situ from readily available phenylsilanes, resulted in 5,6-O-(glucofuranose) and 4,5-O-bridged (fructopyranose) carbohydrates with favoured seven- and eight-membered rings. In these cyclic oligosilyl diethers, three and four ring atoms, respectively, are Si atoms. It is noteworthy, that the seven-membered ring of 5,6-O-[2,4- bis(trimethylsilyl)-1,1,1,3,3,5,5,5-octamethylpentasilan-2,4-diyl]-1, 2-O-isopropylidene-α-D-glucofuranose was expanded to an eight-membered ring by regioselective insertion of aerial oxygen into one of the Si-Si bonds. X-ray analyses of some derivatives are presented.
KW - Bridging protecting groups
KW - Carbohydrates
KW - Hydrodesilylation
KW - Silyl triflates
UR - http://www.scopus.com/inward/record.url?scp=33748328017&partnerID=8YFLogxK
U2 - 10.1055/s-2006-942478
DO - 10.1055/s-2006-942478
M3 - Article
AN - SCOPUS:33748328017
SP - 2685
EP - 2692
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 16
ER -