3′,6′-anhydro-6-O-corynomycoloyl trehalose: Synthesis and identification as the impurity in synthetic cord factor preparations
✍ Scribed by Avraham Liav; Mayer B. Goren
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- English
- Weight
- 370 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
Acylation of 2,3,4,2',3',4'-hexa-O-benzyl-6,6'-di-O-methanesulphonyl-a,tx-trehalose (I) with a reduced amount of potassium corynomycolate yielded a mixture which consisted mainly of 2~3~4~2~3~4~-h~xa-~-benzy~-6-~-~ryn~mye~y~-6~-~-methanesu~ph~ny~-a~-tr~hal~se (2). Catalytic hydrogenolysis of 2 gave the mono-mesylate 4 which was converted into 3',6'-anhydro-6-O-corynomycoloyl-a,tx-trehalose ( 5) by treatment with sodium hydride. The structure of 5 was studied by mass-spectroscopy. Compound 5 was found to be identical with the byproduct obtained in the acylation of6,6'-di-O-p-toluenesulphonyl-a,a-trehalose with potassium corynomycolate.