(2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octanamido-oct-4-ene-1,3-diol | 914784-60-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octanamido-oct-4-ene-1,3-diol
• CAS: 914784-60-4
• 化学式: C₃₂H₄₉NO₃Si
• 分子量: 523.831
• InChiKey: IPVSCDNYHDQKMS-JAPIBCHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  37.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octanamido-oct-4-ene-1,3-diol 、 O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2,6-di-O-benzoyl-β-D-glucopyranosyl)trichloroacetymidate 在 3 A molecular sieve 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以75%的产率得到
  参考文献：
  名称：

  Ganglioside GM₃Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth

  摘要：

  An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C-8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells.

  DOI：

  10.1080/07328300600803518
• 作为产物：
  描述：

  C8-鞘氨醇 在 咪唑 、 三氟化硼乙醚 、 苯硫酚 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octanamido-oct-4-ene-1,3-diol
  参考文献：
  名称：

  Ganglioside GM₃Derivatives with Truncated Ceramide Moiety: Facial Synthesis and Inhibitory Activity against KB Cell Growth

  摘要：

  An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C-8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells.

  DOI：

  10.1080/07328300600803518