Synthesis of benzyl and allyl ethers of D-glucopyranose

Starting from allyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside as a key intermediate, the following crystalline compounds were prepared: 2-O-allyl-3,4,6-tri-O-benzyl-D-glucopyranose (11) and its p-nitrobenzoate; 2,3,5-tri-O-benzyl-D-arabinofuranose (12) and the corresponding arabinitol; allyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (7); 3,4,6-tri-O-benzyl-D-glucopyranose (8); 2-O-allyl-3,4-di-O-benzyl-D-glucopyranose (17) and its bis(p-nitrobenzoate); and 3,4-di-O-benzyl-D-glucopyranose (19). The p-nitrobenzoates of compounds 11 and 17 are potential intermediates for the synthesis of the glycolipids of the cytoplasmic membranes of Streptococci.