3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranose 1-O-trichloroacetamidate | 1233092-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranose 1-O-trichloroacetamidate
• CAS: 1233092-65-3
• 化学式: C₂₈H₃₅Cl₃N₂O₁₁
• 分子量: 681.952
• InChiKey: HJOXCCBFKYHUNN-OSFGTZHUSA-N

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranose 、 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranose 1-O-trichloroacetamidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 以76%的产率得到1-O-acetyl-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
  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
• 作为产物：
  描述：

  3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α,β-D-mannopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-D-mannopyranose 1-O-trichloroacetamidate
  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