(1R,5S)-­1-­dodecoxy-­5-­methyl-­1H-­pyran-­4-­one | 1256569-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1R,5S)-­1-­dodecoxy-­5-­methyl-­1H-­pyran-­4-­one
• 英文别名: (1R,5S)-1-dodecoxy-5-methyl-1H-pyran-4-one；(2R,6S)-2-dodecoxy-6-methyl-2H-pyran-5-one
• CAS: 1256569-28-4
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: IZEZMIOWIOJMOQ-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5S)-­1-­dodecoxy-­5-­methyl-­1H-­pyran-­4-­one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 二正丁基氧化锡 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三苯基膦 、 2,2-二甲氧基丙烷 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 39.17h， 生成 [(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
  参考文献：
  名称：

  Structure–Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity

  摘要：

  Two known cleistriosides and six known cleistetrosides were synthesized and evaluated for anticancer and antibacterial activities. This study, for the first time, reports anticancer activity and comprehensively the antibacterial activity for these oligosaccharide natural products. In addition, two new unnatural cleistetroside analogues were synthesized and tested. Biological activities for the 10 oligosaccharides against B. subtilis were found to range between 4 and >64 mu M and for NCI-H460 human lung cancer epithelial cells between 7.5 and 90.9 mu M. Similar activities were found for seven of the oligosaccharides against the NCI panel of 60 cell lines. The degree of acylation and location of the specific acetate groups had significant effects on the anticancer and antibacterial activity of both the cleistriosides and the cleistetrosides.

  DOI：

  10.1021/ml300303g
• 作为产物：
  描述：

  (2S, 6R)-6-hydroxy-2-methyl-2H-pyran-3(6H)-one 在 4-二甲氨基吡啶 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 (1R,5S)-­1-­dodecoxy-­5-­methyl-­1H-­pyran-­4-­one
  参考文献：
  名称：

  Structure–Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity

  摘要：

  Two known cleistriosides and six known cleistetrosides were synthesized and evaluated for anticancer and antibacterial activities. This study, for the first time, reports anticancer activity and comprehensively the antibacterial activity for these oligosaccharide natural products. In addition, two new unnatural cleistetroside analogues were synthesized and tested. Biological activities for the 10 oligosaccharides against B. subtilis were found to range between 4 and >64 mu M and for NCI-H460 human lung cancer epithelial cells between 7.5 and 90.9 mu M. Similar activities were found for seven of the oligosaccharides against the NCI panel of 60 cell lines. The degree of acylation and location of the specific acetate groups had significant effects on the anticancer and antibacterial activity of both the cleistriosides and the cleistetrosides.

  DOI：

  10.1021/ml300303g

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。
• Structure–Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity
  作者：Pei Shi、Michelle C. Silva、Hua-Yu Leo Wang、Bulan Wu、Novruz G. Akhmedov、Miaosheng Li、Penny J. Beuning、George A. O’Doherty

  DOI：10.1021/ml300303g

  日期：2012.12.13

  Two known cleistriosides and six known cleistetrosides were synthesized and evaluated for anticancer and antibacterial activities. This study, for the first time, reports anticancer activity and comprehensively the antibacterial activity for these oligosaccharide natural products. In addition, two new unnatural cleistetroside analogues were synthesized and tested. Biological activities for the 10 oligosaccharides against B. subtilis were found to range between 4 and >64 mu M and for NCI-H460 human lung cancer epithelial cells between 7.5 and 90.9 mu M. Similar activities were found for seven of the oligosaccharides against the NCI panel of 60 cell lines. The degree of acylation and location of the specific acetate groups had significant effects on the anticancer and antibacterial activity of both the cleistriosides and the cleistetrosides.