A new synthesis of cord factors and analogs

✍ Scribed by A. Liav; M.B. Goren

• Publisher: Elsevier Science
• Year: 1980
• Tongue: English
• Weight: 424 KB
• Volume: 27
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(80)90029-8

✦ Synopsis

Treatment of 6,6t-di-O-trityl-trehalose (1) [2] with benzyl chloride in dioxane followed by acid hydrolysis and chromatography gave the chromatographically pure 2,3,4,2~,3~,4*-hexa-Obenzyl trehalose (2). Compound 2 was converted into the corresponding 6,6'-di-O-methanesulphonyl derivative 3 in quantitative yield. Treatment of the latter compound with the potassium salts of 4-[p-(hexadecyloxy)-phenyl]butyric acid, corynomycollc acid and mycotic acid from Mycobacterium boris afforded the corresponding benzylated-6,6'-di-O-acyl esters 4, 5 and 6 respectively. Catalytic hydtogenolysis of 4, 5, and 6 yielded 6,6'-di-O-4-[p-(hexadecyloxy)-phenyl] butyryl-trehalose 7; 6,6'-di-O-corynomycolyl-trehalose 8; and 6,6~-di~bovi-mycolyl-trehalose 9 respectively.