(2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid | 185118-50-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid
• CAS: 185118-50-7
• 化学式: C₅₂H₈₅N₄O₂₂P
• 分子量: 1149.23
• InChiKey: RYGAFELRXQJLGP-GZSLTIDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  79
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  403
• 氢给体数：
  11
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid 在 sodium periodate 、 氧气 、 sodium acetate 、 臭氧 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (R)-3-{[2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-C-methyl-α-D-glucopyranuronamidosyloxy]hydroxyphosphoryloxy}-2-(2-oxoethoxy)-propionic acid
  参考文献：
  名称：

  Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions

  摘要：

  From moenomycin A both the chromophore part and the Lipid side chain were degraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-position of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with allylic and benzylic halides. With exception of the phytyl bromide-derived reaction product all compounds were antibiotically inactive. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00301-5
• 作为产物：
  描述：

  moenomycin A 在 sodium periodate 、 sodium acetate 、 溶剂黄146 、 硫酸 、 偏二甲肼 作用下， 以 水 、 异丙醇 为溶剂， 反应 9.5h， 以29%的产率得到(2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid
  参考文献：
  名称：

  Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions

  摘要：

  From moenomycin A both the chromophore part and the Lipid side chain were degraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-position of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with allylic and benzylic halides. With exception of the phytyl bromide-derived reaction product all compounds were antibiotically inactive. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00301-5

文献信息

• Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions
  作者：Stefan Vogel、Katherina Stembera、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Peter Welzel、Maxime Lampilas

  DOI：10.1016/s0040-4020(01)00301-5

  日期：2001.5

  From moenomycin A both the chromophore part and the Lipid side chain were degraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-position of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with allylic and benzylic halides. With exception of the phytyl bromide-derived reaction product all compounds were antibiotically inactive. (C) 2001 Elsevier Science Ltd. All rights reserved.