Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

✍ Scribed by Vinodhkumar Subramaniam; Todd L. Lowary

• Book ID: 104209375
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 751 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00260-4

✦ Synopsis

The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl 13-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-ct-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets.