Design and synthesis of mannose analogues as inhibitors of α-mannosidase

Bi- and trivalent glycopeptide mannopyranosides as inhibitors of type 1 fimbriae-mediated bacterial adhesion: variation of valency, aglycon and scaffolding

“…Both carboxy-functionalized mannopyranosides, 5 as well as 6, could be obtained from mannose in four easy steps according to literature-known procedures. [28][29][30] For the preparation of the target glycopeptides, HATU-mediated peptide coupling was employed. First pentapeptide 1 was reacted with the aliphatic carboxylic acid 5, as well as with its benzylic analogue 6 to yield the bivalent glycopeptides 7 and 8, respectively (Scheme 1).…”

Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor

“…Tosylation and subsequent treatment of thiophenyl glycoside 21 29 with dimethoxypropane under acidic conditions gave acetonide 22 in 56% yield. A by-product, thiophenyl 3,6-di-O-tosyl-a-Dmannopyranoside (23), was also isolated in 7% yield from the reaction.…”

The synthesis of d-C-mannopyranosides

“…The cyanoorthoester 3 was first proposed as an intermediate in the activation of the starting substrate. Subsequent isolation and reaction of 3 in the presence of Lewis acids gave the same product, however with lower yields and selectivity (Scheme 9) [62,96,105].…”

“…Various D-Cmannopyranoside derivatives have been synthesized in order to evaluate their biological activity as lectin inhibitors relative to their O-glycoside counterpart [41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57]. C-mannosides have also been prepared and tested as potential glycosidase and glycosyltransferase inhibitors [58][59][60][61][62][63][64], as anti-inflammatory derivatives [65], anti-tumor agents [30,66], and anti-bacterial agents [67,68].…”