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)-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside | 1334393-36-0

• 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)-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside
• CAS: 1334393-36-0
• 化学式: C₁₁₄H₁₁₈O₂₆
• 分子量: 1904.18
• InChiKey: LTGSPOKPLFMPDY-PMPXKOKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.89
• 重原子数：
  140.0
• 可旋转键数：
  29.0
• 环数：
  18.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  310.54
• 氢给体数：
  0.0
• 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)-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside 在 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以87%的产率得到
  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：

  perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 、 betulinic acid 3β-O-3'-O-allyl-4',6'-O-benzylidene-β-D-glucopyranoside 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 1.5h， 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)-3'-O-allyl-4',6'-O-benzylidene-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