5-(methoxycarbonyl)pentyl 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside | 1233092-74-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(methoxycarbonyl)pentyl 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside
• CAS: 1233092-74-4
• 化学式: C₇₅H₁₀₁N₃O₂₉
• 分子量: 1508.63
• InChiKey: WCHDUAUHMGUUGK-FCVWXIHWSA-N

反应信息

• 作为产物：
  描述：

  5-(methoxycarbonyl)pentyl 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside 、 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulonoyl-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranose 1-O-trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以6.22 g的产率得到5-(methoxycarbonyl)pentyl 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Enhanced stereoselectivity of α-mannosylation under thermodynamic control using trichloroacetimidates

  摘要：

  O-Specific polysaccharides of Vibrio cholerae 01, serotypes Inaba and Ogawa, consist of alpha-(1-2)-linked N-(3-deoxy-L-glycero-tetronyl)perosamine (4-amino-4,6-dideoxy-D-mannose) The blockwise synthesis of larger fragments of such O-PSs involves oligosaccharide glycosyl donors that contain a nonparticipating 2-O-glycosyl group at the position vicinal to the anomeric center where the new glycosidic linkage is formed Such glycosyl donors may bear at C-4 either a latent acylamino (e g, azido) or the 3-deoxy-L-glycero-tetronamido group. While monosaccharide glycosyl donors, even those bearing a nonparticipating group at O-2 (e g, methyl), and the 4-N-(3-deoxy-L-glycero-tetronyl) side chain form alpha-linked oligosaccharides with excellent stereoselectivity, alpha-mannosylation with analogous oligosaccharide donors in this series is adversely affected by the presence of the side chain Consequently, the unwanted beta-product is formed in a considerable amount Conducting the reaction at elevated temperature under thermodynamic control substantially enhances formation of the alpha-linked oligosaccharide This effect is much more pronounced when glycosyl trichloroacetimidates, rather than thioglycosides or glycosyl chlorides, are used as glycosyl donors Published by Elsevier Ltd

  DOI：

  10.1016/j.carres.2010.03.025