allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside | 342636-75-3

• 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: allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 342636-75-3
• 化学式: C₅₆H₈₈Cl₃NO₁₀Si
• 分子量: 1069.76
• InChiKey: WYXYPFUUADMMSU-KZKLCEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.15
• 重原子数：
  71
• 可旋转键数：
  40
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranoside 在 四氮唑 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 11.5h， 生成 6-O-(tert-butyldiphenylsilyl)-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-D-glucopyranose
  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：

  [(4aR,6S,7R,8R,8aS)-2,2-dimethyl-6-prop-2-enoxy-7-(2,2,2-trichloroethoxycarbonylamino)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] (3R)-3-tetradecanoyloxytetradecanoate 、 叔丁基二苯基氯硅烷 在 对甲苯磺酸 、 咪唑 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到allyl 6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-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