allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside | 607364-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside
• 英文别名: Bz(-2)[TBDMS(-3)][Bz(-6)]Glc(a)-O-allyl；[(2R,3R,4S,5R,6S)-5-benzoyloxy-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-6-prop-2-enoxyoxan-2-yl]methyl benzoate
• CAS: 607364-83-0
• 化学式: C₂₉H₃₈O₈Si
• 分子量: 542.701
• InChiKey: UFEQGCRZWKSMLW-MOBZEUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 allyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1->4)-2,6-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Laminarin Oligosaccharide Derivatives Havingd‐Arabinofuranosyl Side‐Chains

  摘要：

  An efficient glycosylation strategy was applied in the synthesis of beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->4)]-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->6)]-D-glucopyranose to secure beta-D-(1-->3) glycosidic bond formation between glucopyranosyl residues. The new strategy using a 4,6-O-benzylidenated acceptor avoided generation of the alpha major isomer in the attempted beta-D-(1-->3) glycosylation under standard glycosylation conditions. The hexasaccharide we prepared showed about 30% tumor growth inhibition towards S180 model study.

  DOI：

  10.1081/car-120023470
• 作为产物：
  描述：

  Allyl 2,6-di-O-benzoyl-α-D-glucopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以69%的产率得到allyl 2,6-di-O-benzoyl-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Laminarin Oligosaccharide Derivatives Havingd‐Arabinofuranosyl Side‐Chains

  摘要：

  An efficient glycosylation strategy was applied in the synthesis of beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->4)]-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->6)]-D-glucopyranose to secure beta-D-(1-->3) glycosidic bond formation between glucopyranosyl residues. The new strategy using a 4,6-O-benzylidenated acceptor avoided generation of the alpha major isomer in the attempted beta-D-(1-->3) glycosylation under standard glycosylation conditions. The hexasaccharide we prepared showed about 30% tumor growth inhibition towards S180 model study.

  DOI：

  10.1081/car-120023470

文献信息

• Synthesis of Laminarin Oligosaccharide Derivatives Having<scp>d</scp>‐Arabinofuranosyl Side‐Chains
  作者：Hongmei He、Guofeng Gu、Yuguo Du

  DOI：10.1081/car-120023470

  日期：2003.1.8

  An efficient glycosylation strategy was applied in the synthesis of beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->4)]-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[alpha-D-arabinopyranosyl-(1-->6)]-D-glucopyranose to secure beta-D-(1-->3) glycosidic bond formation between glucopyranosyl residues. The new strategy using a 4,6-O-benzylidenated acceptor avoided generation of the alpha major isomer in the attempted beta-D-(1-->3) glycosylation under standard glycosylation conditions. The hexasaccharide we prepared showed about 30% tumor growth inhibition towards S180 model study.