cholesteryl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside | 125344-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4R,6R)-3,4-diacetyloxy-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 125344-66-3
• 化学式: C₃₉H₆₂O₈
• 分子量: 658.916
• InChiKey: GILDPYIHJYEQDT-TZDKTMBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  胆固醇 、 [(2R,3R,4R,6S)-3,4-diacetyloxy-6-chlorooxan-2-yl]methyl acetate 生成 cholesteryl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  PETROVIC, JULIJANA;SCANADI, JANOS;CANADI, DERD;PETROVIC, IVANKA;MILJKOVIC+, J. SERB. CHEM. SOC., 54,(1989) N, C. 229-232

  摘要：

  DOI：

文献信息

• Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using <i>S</i>-But-3-ynyl Thioglycoside Donors
  作者：Surya Adhikari、Kedar N. Baryal、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1021/cs300670k

  日期：2013.1.4

  A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy alpha-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2-deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford alpha-selective glycosides in good to excellent yields.
• α-Selective synthesis of 2-deoxy-glycosides and disaccharides
  作者：Guofang Yang、Xiaosheng Luo、Hong Guo、Qingbing Wang、Jiafen Zhou、Tianyun Huang、Jie Tang、Junjie Shan、Jianbo Zhang

  DOI：10.1080/07328303.2018.1439498

  日期：2018.3.24

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.