(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 2-amino-2-deoxy-4-O-(diallylphosphono)-6-O-(tert-butyldiphenylsilyl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside | 482635-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 2-amino-2-deoxy-4-O-(diallylphosphono)-6-O-(tert-butyldiphenylsilyl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5S,6R)-3-amino-5-bis(prop-2-enoxy)phosphoryloxy-2-[(E,2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(octadecanoylamino)octadec-4-enoxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 482635-12-1
• 化学式: C₉₈H₁₇₅N₂O₁₃PSi₂
• 分子量: 1676.62
• InChiKey: UMNSTRYGHHULSS-RSUFSWQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.76
• 重原子数：
  116
• 可旋转键数：
  79
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  189
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-butyldimethylsilyloxy)tetradecanoic acid 、 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 2-amino-2-deoxy-4-O-(diallylphosphono)-6-O-(tert-butyldiphenylsilyl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-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 24.0h， 以60%的产率得到(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 2-[(R)-3-(tert-butyldimethylsilyloxy)tetradecanoylamino]-6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-gluco...
  参考文献：
  名称：

  Synthesis of ceramidated GLA-60 derivatives

  摘要：

  Ceramidated GLA-60 derivatives 11 and 11' were synthesized from I via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00179-9
• 作为产物：
  描述：

  (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranoside 在 氯化铵 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)octadec-4-enyl 2-amino-2-deoxy-4-O-(diallylphosphono)-6-O-(tert-butyldiphenylsilyl)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ceramidated GLA-60 derivatives

  摘要：

  Ceramidated GLA-60 derivatives 11 and 11' were synthesized from I via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00179-9