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Cord-factor analogs: synthesis of 6,6′-di-O-mycoloyl- and -corynomycoloyl-(α-d-galactopyranosyl α-d-galactopyranoside)

✍ Scribed by Avraham Liav; Harold M. Flowers; Mayer B. Goren

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
445 KB
Volume
133
Category
Article
ISSN
0008-6215

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✦ Synopsis

Appropriate solvolysis of 2,3,2',3'-tetra-O-benzyl-4,6,4',6'-tetra-O-mesyla,a-trehalose gave 2,3,2',3'-tetra-O-benzyl-(a-D-galactopyranosyl a-D-galactopyranoside) (2). Selective tosylation or mesylation of 2 respectively gave the 6,6'ditosylate (3) and 6,6'-dimesylate (4), the structures of which were confirmed by the 'H-n.m.r. spectra of the corresponding 4,4'-di-0-acetyl derivatives. Treatment of 3 with potassium mycolate in toluene, and subsequent hydrogenolysis, gave the 6'-mycolate 6-tosylate derivative. Treatment of 3 with potassium mycolate or potassium corynomycolate in hexamethylphosphoric triamide, followed by catalytic hydrogenolysis, yielded the respective cord-factor analogs 6,6'-di-O-mycoloyl-(cr-Dgalactopyranosyl a-D-galactopyranoside) and 6,6'-di-0-corynomycoloyl-((Y-Dgalactopyranosyl a-D-galactopyranoside).

The same 6,6'-diesters were obtained from the 6,6'-dimesylate 4. Putative 4,6-anhydro-6'-monomycolates are also described.

halose) was replaced by the corresponding D-mul~110 disaccharide2.

We now describe the synthesis, from a,a-trehalose, of a suitably blocked cu-D-galactopyranosyl cu-D-galactopyranoside derivative, and its conversion into *Visiting scientist from the Weizmann Institute of Science. Rehovot, Israel.

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