108167-19-7

Upstream product

• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 34957-73-8 methyl 9-hydroxynonanoate 
• 86861-46-3 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl bromide 

Downstream Products

• 108167-20-0 8-(methoxycarbonyl)octyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 134040-48-5 8-methoxycarbonyloctyl 2,4-di-O-benzyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 
• 134040-46-3 8-methoxycarbonyloctyl 2,4-di-O-benzyl-3,6-di-O-p-nitrobenzoyl-β-D-mannopyranoside 
• 134040-45-2 8-methoxycarbonyloctyl 2,4-di-O-benzyl-3,6-di-O-p-nitrobenzoyl-α-D-mannopyranoside 
• 134040-47-4 8-methoxycarbonyloctyl 2,4-di-O-benzyl-β-D-mannopyranoside 

Relevant academic research and scientific papers

Use of N-acetylglucosaminyltransferases I and II in the preparative synthesis of oligosaccharides.

8-Methoxycarbonyloctyl 3,5-di-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside (1) has been synthesised chemically. Compound 1 is a substrate for N-acetylglucosaminyltransferase-I (GlcNAcT-I), which transfers a beta-D-GlcpNAc residue from UDP-GlcpNAc to position 2 of the alpha-Man-(1----3) unit to produce 2. In turn, the tetrasaccharide 2 is an acceptor for GlcNAcT-II which, in the presence of UDP-GlcpNAc, converts 2 into 8-methoxycarbonyloctyl 3,6-di-O-[2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D- mannopyranosyl]-beta-D-mannopyranoside (3). These conversions were carried out on a 50-100 mg scale using enzyme preparations obtained from rabbit liver in a single step by affinity chromatography.

Synthesis of Phosphorylated Pentasaccharides Found on Asparagine-Linked Carbohydrate Chains of Lysosomal Enzymes

Simple and direct syntheses of 8-(methoxycarbonyl)octyl 3,6-bis-O-2-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl-α-D-mannopyranoside (2), The corresponding terminally 6-O-diphosphorylated pentasaccharide 3, and the two terminally 6-O-monophosphorylated deri