Total Synthesis of a Trehalose-Containing Lipooligosaccharide Analogue from Mycobacterium linda

HO HO OH Regioselective [2+2] Glycosylation OH HO OH HO-\ HO HO OH HO OH HO a,a-D-Trehalose OH F Regioselective [1+1] Glycosylation 0 OC15H31 ,1O OH HO C.I51-131 0 H31O15 0 310150 Consecutive Regioselective Acylations ABSTRACT: A short and efficient methodology has been developed to synthesize an analogue of a lipooligosaccharide from Mycobacterium linda isolated from Crohn's disease. The total synthesis of the tetrasaccharide was achieved via a convergent [2 + 2] glycosylation approach. The key features of the synthesis involve the selective functionalization of a trehalose core via highly regioselective acylations and regioselective glycosylations. The synthesis was completed via a longest linear sequence of 14 steps in a 14.2% overall yield.

Automated summary

This article introduces a simple method for synthesizing a lipooligosaccharide analogue from Mycobacterium linda isolated from Crohn's disease. The total synthesis of the tetrasaccharide was achieved through a [2+2] glycosylation reaction, with the key features being the selective functionalization of a trehalose core via highly regioselective acylations and regioselective glycosylations. The synthesis was completed in a longest linear sequence of 14 steps with an overall yield of 14.2%.