betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside | 1104398-66-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-6-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
• CAS: 1104398-66-4
• 化学式: C₅₇H₇₂O₉
• 分子量: 901.193
• InChiKey: HVHLPTLJSPZFSK-MURJDFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  66
• 可旋转键数：
  13
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 silver trifluoromethanesulfonate 作用下， 生成 allobetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins

  摘要：

  The naturally occurring cytotoxic saponin 28-O-beta-D-glucopyranosylbetulinic acid 3 beta-O-alpha-L-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-L-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC50 1.8-1.9 mu M).

  DOI：

  10.1021/np800579x
• 作为产物：
  描述：

  28-O-tert-butyldiphenylsilylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以87%的产率得到betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins

  摘要：

  The naturally occurring cytotoxic saponin 28-O-beta-D-glucopyranosylbetulinic acid 3 beta-O-alpha-L-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-L-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC50 1.8-1.9 mu M).

  DOI：

  10.1021/np800579x

文献信息

• Efficient Synthesis of Lupane-Type Saponins via Gold(I)-Catalyzed Glycosylation with Glycosyl <i>ortho</i>-Alkynylbenzoates as Donors
  作者：Yan Li、Jiansong Sun、Biao Yu

  DOI：10.1021/ol202232v

  日期：2011.10.21

  Glycosylation of the acid labile betulin and betulinic acid derivatives was achieved with glycosyl ortho-hexynyibenzoates as donors under the catalysis of PPh3AuNTf2; this enabled the efficient synthesis of lupane-type saponins, as exemplified by the total synthesis of the proposed betulinic acid trisaccharide from Bersama engleriana.
• Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins
  作者：Charles Gauthier、Jean Legault、Serge Lavoie、Simon Rondeau、Samuel Tremblay、André Pichette

  DOI：10.1021/np800579x

  日期：2009.1.23

  The naturally occurring cytotoxic saponin 28-O-beta-D-glucopyranosylbetulinic acid 3 beta-O-alpha-L-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-L-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC50 1.8-1.9 mu M).