(10R)-2-nonadecanone-10-yl 6-deoxy-α-L-glucopyranosyl-(1->2)-[6-deoxy-β-D-talopyranosyl-(1->6)]-3,4-di-O-butyryl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside | 876687-39-7

• 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: (10R)-2-nonadecanone-10-yl 6-deoxy-α-L-glucopyranosyl-(1->2)-[6-deoxy-β-D-talopyranosyl-(1->6)]-3,4-di-O-butyryl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
• 英文别名: caminoside B；[(2R,3R,4S,5R,6S)-4-butanoyloxy-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(10R)-2-oxononadecan-10-yl]oxyoxan-3-yl]oxy-5-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] butanoate
• CAS: 876687-39-7
• 化学式: C₅₁H₉₀O₂₂
• 分子量: 1055.26
• InChiKey: HMMLFRBQPRRQSQ-NLKXDBGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  73
• 可旋转键数：
  34
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  326
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (10R)-2-nonadecanone-10-yl 6-deoxy-α-L-glucopyranosyl-(1->2)-[6-deoxy-β-D-talopyranosyl-(1->6)]-3,4-di-O-butyryl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 18.0h， 生成 [(2R,3R,4S,5R,6S)-4-butanoyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-[(10R)-2-oxononadecan-10-yl]oxyoxan-3-yl]oxy-5-[(2S,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-2-[[(2R,3S,4S,5S,6R)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] butanoate
  参考文献：
  名称：

  Caminosides B−D, Antimicrobial Glycolipids Isolated from the Marine Sponge Caminus sphaeroconia

  摘要：

  A screening pro-rain aimed at discovering inhibitors of the bacterial type III secretion system identified the MeOH extract of the Caribbean sponge Caminus sphaeroconia as an active hit in the initial assay. Bioassay-guided fractionation of the crude extract. led to the isolation of caminosides A (1) to D (4), a family of antimicrobial glycolipids. The structures of the three new caminosides B (2) to D (4) have been elucidated by spectroscopic analysis.

  DOI：

  10.1021/np050192h
• 作为产物：
  描述：

  (10R)-2-nonadecanone-10-yl 2,3,4-tri-O-benzyl-6-deoxy-α-L-glucopyranosyl-(1->2)-[2,3,4-tri-O-benzyl-6-deoxy-β-D-talopyranosyl-(1->6)]-3,4-di-O-butyryl-β-D-glucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以88%的产率得到(10R)-2-nonadecanone-10-yl 6-deoxy-α-L-glucopyranosyl-(1->2)-[6-deoxy-β-D-talopyranosyl-(1->6)]-3,4-di-O-butyryl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
  参考文献：
  名称：

  从海洋海绵卡米氏球菌中分离出的新型抗菌糖脂caminoside B的全合成

  摘要：

  开发了首个全合成的caminoside B，一种从海洋海绵体Caminus sphaeroconia分离出的新型海洋抗菌糖脂。这种海洋小分子抑制剂（IC（50）= 20 microM）靶向细菌发病机理的III型分泌途径是通过基于两个糖苷键立体控制结构的'2 + 2 + 1'策略以高产量组装的。

  DOI：

  10.1016/j.carres.2010.01.015