α-D-oleandrose | 99437-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-oleandrose
• 英文别名: α-D-oleandropyranose；(2S,4R,5R,6R)-4-methoxy-6-methyloxane-2,5-diol
• CAS: 99437-07-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: DBDJCJKVEBFXHG-MVIOUDGNSA-N

物化性质

• 沸点：
  288.7±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二异氰酸硝基苯 、 α-D-oleandrose 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (3,5-Dinitro-phenyl)-carbamic acid (4R,5R,6R)-5-hydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Tsukamoto, Sachiko; Hayashi, Koji; Kaneko, Ko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2625 - 2632

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-Butyl-((2S,3S,4S,6R)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 在 四丁基氟化铵 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 α-D-oleandrose
  参考文献：
  名称：

  Dornhagen, Juergen; Klausener, Alexander; Runsink, Jan, Liebigs Annalen der Chemie, 1985, # 9, p. 1838 - 1846

  摘要：

  DOI：

文献信息

• Structure determination of two new C₂₁ steroidal glycosides from <i>Cynanchum komarovii</i>
  作者：Dan Zhao、Ming-Xu Tang、Shan-Shan Su、Xiao-Jie Lu、Yu-Bo Wang、Shao-Fei Chen、Hai-Feng Wang、Gang Chen、Yue-Hu Pei

  DOI：10.1080/10286020.2017.1396977

  日期：2018.9.2

  Two new 13,14:14,15-disecopregnane-type C21 steroidal glycosides, namely komarosides R (1) and S (2), along with four known compounds (3–6), were obtained from the 95% ethanol extract of the whole herbs of Cynanchum komarovii Al.Iljinski (Asclepiadaceae). The structures of new compounds were elucidated on the basis of 1D, 2D NMR spectroscopic data and acid hydrolysis. Compounds 1 and 2 showed potent

  两个新的13,14-：14,15- disecopregnane-C型21个甾体糖苷，即komarosides R（1）和S（2），具有四个已知化合物（沿3 - 6），是从的95％乙醇提取物得到Cynanchum komarovii Al.Iljinski的全部草药。在1D，2D NMR光谱数据和酸水解的基础上阐明了新化合物的结构。与阳性对照5-氟尿嘧啶（6.4μM）相比，化合物1和2对人白血病细胞系（HL-60）表现出强抑制活性，IC 50值分别为6.2和17.6μM。
• An appraisal of oxoketene cycloaddition methodology for the synthesis of 2,6-dideoxysugars and fluorinated 2,6-dideoxysugars
  作者：Christophe Audouard、Kim Bettaney (née Middleton)、Châu T. Doan、Giuseppe Rinaudo、Peter J. Jervis、Jonathan M. Percy

  DOI：10.1039/b817672h

  日期：——

  The cycloaddition reaction of acylketenes with vinyl ethers affords an extremely direct route to 2,6-dideoxysugars and their methyl ethers. The lithium enolate of commercial 2,6,6-trimethyldioxinone 3 was fluorinated in good yield to afford fluorinated dioxinone 8. An illustrative range of fluorinated 2,6-dideoxysugar derivatives was prepared via the acetyl ketene–vinyl ether cycloadduct. Electronic

  酰基乙烯酮与乙烯基醚的环加成反应提供了一条直接的途径来制备2，6-二脱氧糖及其甲基醚。商业化的2,6,6-三甲基二恶英酮3的烯醇锂以良好的产率被氟化，得到氟化的二恶英酮8。通过乙酰基乙烯酮-乙烯基醚环加合物制备了一系列示例性的氟化2,6-二脱氧糖衍生物。进行电子结构计算以研究氟原子对（氟乙酰基）乙烯酮反应性中间体的易于形成和随后反应的影响。单个氟原子可降低约25％的片段化势垒。7.5 kJ摩尔-1，与实验结果一致，但对确定乙烯基醚添加速率或氧杂环丁烯二聚化的障碍几乎没有影响。
• Bioactive C₂₁ Steroidal Glycosides from the Roots of <i>Cynanchum otophyllum</i> That Suppress the Seizure-like Locomotor Activity of Zebrafish Caused by Pentylenetetrazole
  作者：Jin-Long Li、Juan Zhou、Zhen-Hua Chen、Sheng-Ya Guo、Chun-Qi Li、Wei-Min Zhao

  DOI：10.1021/np501058b

  日期：2015.7.24

  Six new C-21 steroidal glycosides, cynotophyllosides A-F (1-6), together with 16 known compounds, were isolated from the roots of Cynanchum otophyllum. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The three major components, otophylloside F (15), otophylloside B (17), and rostratamine 3-O-beta-D-oleandropyranosyl-(1 beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl (1 -> 4)-beta-D-cymaropyranoside), suppressed the seizure-like locomotor activity caused by pentylenetetrazole in zebrafish. Preliminary structure-activity relation studies revealed that a pregnene skeleton with a C-12 ester group (ikemaoyl > cinnamoyl > hydroxy > p-hydroxybenzoyl) and a C-3 sugar chain consisting of three 2,6-dideoxysaccharide units is essential for this suppressive activity.
• Pedersen, Christian; Jensen, Hanne Stampe, Acta Chemica Scandinavica, 1994, vol. 48, # 3, p. 222 - 227
  作者：Pedersen, Christian、Jensen, Hanne Stampe

  DOI：——

  日期：——
• TRIVEDI, RASHMI;KHARE, ANAKSHI;KHARE, MAHESHWARI P., PHYTOCHEMISTRY., 28,(1989) N, C. 1211-1213
  作者：TRIVEDI, RASHMI、KHARE, ANAKSHI、KHARE, MAHESHWARI P.

  DOI：——

  日期：——