1-O-dodecanyl-2,4-di-O-acetyl-α-rhamnopyranosyl-(1->3)-4-O-acetyl-α-rhamnopyranosyl-(1->4)-α-rhamnopyranoside | 882658-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-dodecanyl-2,4-di-O-acetyl-α-rhamnopyranosyl-(1->3)-4-O-acetyl-α-rhamnopyranosyl-(1->4)-α-rhamnopyranoside
• 英文别名: cleistrioside-5；cleistetroside-5；dodecyl 2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-α-L-rhamnopyranosyl-(1->4)-α-L-rhamnopyranoside；[(2S,3R,4R,5R,6S)-5-acetyloxy-6-[(2S,3R,4S,5S,6S)-5-acetyloxy-2-[(2S,3R,4S,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-3-hydroxy-6-methyloxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 882658-98-2
• 化学式: C₃₆H₆₂O₁₆
• 分子量: 750.879
• InChiKey: DFGWXZRIFMDDNA-DAZFWBFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  215
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-O-dodecanyl-2,4-di-O-acetyl-α-rhamnopyranosyl-(1->3)-4-O-acetyl-α-rhamnopyranosyl-(1->4)-α-rhamnopyranoside 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到dodecyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives

  摘要：

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.028
• 作为产物：
  描述：

  [(2S,3S,4S,5R,6S)-6-[[(3aR,4R,6S,7S,7aR)-4-dodecoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-5-hydroxy-2-methyl-4-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-3-yl] acetate 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 水 、 四丁基碘化铵 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 硫脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 35.66h， 生成 1-O-dodecanyl-2,4-di-O-acetyl-α-rhamnopyranosyl-(1->3)-4-O-acetyl-α-rhamnopyranosyl-(1->4)-α-rhamnopyranoside
  参考文献：
  名称：

  通过不同的 De Novo 不对称方法合成几种 Cleistrioside 和 Cleistetroside 天然产物

  摘要：

  已经实现了几种部分酰化的十二烷基三和四鼠李糖苷天然产物（cleistriosides- 5和6和 cleistetrosides- 2至7）的从头不对称合成（19-24 步）。不同的路线需要使用三个或更少的保护基团。不对称性是通过酰基呋喃的 Noyori 还原得出的。通过非对映选择性钯催化的糖基化、酮还原和二羟基化来安装鼠李糖立体化学。

  DOI：

  10.1021/ol1023344

文献信息

• Synthesis of Several Cleistrioside and Cleistetroside Natural Products via a Divergent De Novo Asymmetric Approach
  作者：Bulan Wu、Miaosheng Li、George A. O’Doherty

  DOI：10.1021/ol1023344

  日期：2010.12.3

  The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19−24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective

  已经实现了几种部分酰化的十二烷基三和四鼠李糖苷天然产物（cleistriosides- 5和6和 cleistetrosides- 2至7）的从头不对称合成（19-24 步）。不同的路线需要使用三个或更少的保护基团。不对称性是通过酰基呋喃的 Noyori 还原得出的。通过非对映选择性钯催化的糖基化、酮还原和二羟基化来安装鼠李糖立体化学。
• Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives
  作者：Ning Ding、Zaihong Zhang、Wei Zhang、Yuexing Chun、Peng Wang、Huimin Qi、Shan Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.07.028

  日期：2011.10

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.