Synthesis of pentaarabinofuranosyl structure motif A of Mycobacterium tuberculosis

A Versatile Synthesis of Pentacosafuranoside Subunit Reminiscent of Mycobacterial Arabinogalactan Employing One Strategic Glycosidation Protocol

“…The glycosyl donor was set out easily from two starting substrates 9 and 10 (Scheme ). The synthetic effort started with a known arabinofuranoside 11 the isopropylidene group of which was opened with allyl alcohol under acidic conditions to afford a separable mixture of allyl arabinofuranosides 12 α and 12 β in 1:1 ratio, which are utilised as glycosyl acceptors later . 1,2‐ cis ‐Arabinofuranosylation was envisioned through oxidation‐reduction strategy; hence, the 1, 2‐ trans ‐furanosyl donor of Rib f was required.…”

d-ARABINOFURANOSIDES FROM MYCOBACTERIA: SYNTHESIS AND CONFORMATION

“…On the other hand, reaction of the pyridyl thioglycoside 34 with alcohol 57 has been shown [76] to provide good yields of the b-linked disaccharide 58 (Figure 17). No mention was made of the formation of any a-glycoside product in this glycosylation reaction.…”

“…These include glycosyl acetates 26 [69] and 27, [70,71] glycosyl halides 28, [68,72] 29, [49] 30, [73] 31, [73] and thioglycosides 32-34. [55,[74][75][76] …”

Studies toward the Development of Anti-Tuberculosis Vaccines Based on Mycobacterial Lipoarabinomannan

“…With regard to the synthesis of terminal fragments, hexasaccharide 1 has been synthesized as its methyl (31,32,33) and 8-aminooctyl glycoside (34). Related pentasaccharide (35,36) and octasaccharide (37) derivatives, all containing the key β-arabinofiiranosyl residues, have also been synthesized. Finally, oligosaccharides containing the capping units have been prepared.…”