Oxazoline synthesis of 1,2-trans-2-acetamido-2-deoxyglycosides

Add time:07/14/2019    Source:sciencedirect.com

The glycosylating activity of 2-methyl-glyco[1′,2′:4,5]- 2-oxazolines has been investigated in connection with the synthesis of 1,2-trans-2-acetamido-2-deoxy-glycosides. Treatment of 2-methyl-4,5-(3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyrano)-2-oxazoline (1) and 2-methyl-4,5-[4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyrano]-2-oxazoline (2) with p-nitrophenyl 2-acetamido-3,4-di-O-acetyl- (3) and p-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside (4) in the presence of catalytic amounts of toluene-p-sulphonic acid gives p-nitrophenyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside (7), p-nitrophenyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-β-D-glucopyranoside (9), and p-nitrophenyl O-(2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)- O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside (11) in yields of up to 50%.

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