2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranoside | 503830-09-9

• 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: 2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranoside
• CAS: 503830-09-9
• 化学式: C₃₈H₄₅NO₉Si
• 分子量: 687.862
• InChiKey: LKTXRKFCMXBJAV-KGOFVWAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117.67
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1
• 作为产物：
  描述：

  乙酰丙酸 、 2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1