chapter  32
6 Pages

Synthesis of 4-Methoxyphenyl α-d-Rhamnopyranoside

ByTze Chieh Shiao, Sylvain Rocheleau, René Roy

Thus, starting from unprotected d-mannopyranoside 1,8,9 its direct conversion to the 6-deoxy-6-iodo-derivative 2 using the Garegg-Samuelsson’s procedure (I2, Ph3P, imidazole, THF)10 occurred uneventfully in 93% yield according to the general Scheme. Radical dehalogenation using tri-n-butyltin hydride in the presence

Experimental Methods ........................................................................................... 252 General Methods ............................................................................................... 252

4-Methoxyphenyl 6-Deoxy-6-iodo-α-d-mannopyranoside (2) .................... 252 4-Methoxyphenyl α-d-Rhamnopyranoside (4-Methoxyphenyl 6-Deoxyα-d-Mannopyranoside) (3) ........................................................................... 253

Acknowledgments .................................................................................................. 253 References .............................................................................................................. 255

d-rhamnopyranoside 3 in 94% yield after silica gel column chromatography. Notably, we report herein its Nuclear Magnetic Resonance (NMR) spectra both in CD3OD and in CDCl3, the latter showing a rst-order spectrum.