28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside | 1104398-84-6

• 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: 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-[(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methoxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1104398-84-6
• 化学式: C₉₁H₉₈O₁₈
• 分子量: 1479.77
• InChiKey: WNJVFPLMMWDHDT-MUPFVLHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.7
• 重原子数：
  109
• 可旋转键数：
  28
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到28-O-β-D-glucopyranosylbetulin 3β-O-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：

  perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 、 betulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulin 3β-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient Synthesis of Lupane-Type Saponins via Gold(I)-Catalyzed Glycosylation with Glycosyl ortho-Alkynylbenzoates as Donors

  摘要：

  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.

  DOI：

  10.1021/ol202232v