28-O-2"',3"',4"',6"'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2",3",4",6"-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside | 1334393-40-6

• 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-glucopyranosylbetulinate 3β-O-2",3",4",6"-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
• CAS: 1334393-40-6
• 化学式: C₁₀₄H₁₁₀O₂₆
• 分子量: 1776.0
• InChiKey: SGRMDGSLSAZVPO-LSCOPHTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.91
• 重原子数：
  130.0
• 可旋转键数：
  26.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  343.54
• 氢给体数：
  3.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  28-O-2"',3"',4"',6"'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2",3",4",6"-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到28-O-2"',3"',4"',6"'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2",3",4",6"-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
  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
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到28-O-2"',3"',4"',6"'-tetra-O-benzoyl-β-D-glucopyranosylbetulinate 3β-O-2",3",4",6"-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside
  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