Phenyl 2-O-acetyl-3-O-allyl-4-O-benzyl-1-thio-β-d- glucopyranoside, a Versatile, Orthogonally Protected Building Block

It has always been of high interest to prepare orthogonally protected monosaccharides. To date, there are only a few examples in the literature of d-glucose protected with four different functionalities.2 We have recently developed a practical eight-step synthesis (Scheme 24.1) of such substance from commercially available diacetoned-glucose, which does not require chromatographic purication.