1-O-dodecanyl-2,3-O-isopropylidene-α-L-rhamnopyranoside | 943221-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-dodecanyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: dodecanyl 2,3-O-isopropylidene-α-L-rhamnopyranoside；(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-ol
• CAS: 943221-76-9
• 化学式: C₂₁H₄₀O₅
• 分子量: 372.546
• InChiKey: XLOKFKMSWCKQGB-CENDIDJXSA-N

物化性质

• 熔点：
  56.0-57.2 °C
• 沸点：
  471.1±45.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-dodecanyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 水 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 27.17h， 生成
  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
• 作为产物：
  描述：

  (1R,5S)-­1-­dodecoxy-­5-­methyl-­1H-­pyran-­4-­one 在 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 水 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 18.0h， 生成 1-O-dodecanyl-2,3-O-isopropylidene-α-L-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

• 一种鼠李糖苷类化合物及其作为抗多药耐药 肿瘤药物的应用
  申请人：扬州蓝色生物医药科技有限公司

  公开号：CN105085585B

  公开（公告）日：2019-02-05

  本发明涉及一种鼠李糖苷类化合物及其作为抗多药耐药肿瘤药物的应用。本发明化合物对敏感肿瘤细胞株KB、MCF‑7的细胞毒活性与阳性对照药(阿霉素、长春新碱、紫杉醇)活性相当，对耐药肿瘤细胞株KB/VCR、MCF‑7/ADR的细胞毒活性强于阳性对照药；且本发明化合物的水溶性较好。本发明化合物有望发展为新型抗肿瘤药物。
• Total synthesis of cleistetroside-2, partially acetylated dodecanyl tetrarhamnoside derivative isolated from Cleistopholis patens and Cleistopholis glauca
  作者：Zaihong Zhang、Peng Wang、Ning Ding、Gaopeng Song、Yingxia Li

  DOI：10.1016/j.carres.2007.03.014

  日期：2007.7

  The total synthesis of a partially acetylated dodecanyl tetrarhamnoside derivative, cleistetroside-2, which was isolated from Cleistopholis patens and Cleistopholis glauca and showed significant in vitro antibacterial activity against the Gram-positive bacteria, was achieved for the first time.

  首次实现了部分乙酰化的十二烷基四鼠李糖苷衍生物cleistetroside-2的总合成，该衍生物是从Cleistopholis patens和Cleistopholis glauca中分离出来的，并且对革兰氏阳性细菌显示出显着的体外抗菌活性。
• 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.
• Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens
  作者：Lijian Cheng、Qi Chen、Yuguo Du

  DOI：10.1016/j.carres.2007.05.019

  日期：2007.8

  A tetrasaccharide, dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-alpha-L-rhamnopyranoside (cleistetroside-2), was synthesized via '2+2' convergent strategy. Sequential regioselective 3-O-glycosylation of isopropyl 1-thio-alpha-L-rhamnopyranoside (4) with 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl trichloroacetimidate (8), and isopropyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-1-thio-rh amnopyranoside (10) with dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-2,3-O-isopropylidene-alpha-L-rharnnopyranoside (12), greatly facilitate the target availability. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.