28-O-allyl-oleanate-3-yl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 562834-45-1

• 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-allyl-oleanate-3-yl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: prop-2-enyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 562834-45-1
• 化学式: C₅₃H₇₁NO₁₂
• 分子量: 914.146
• InChiKey: KVYJULBRHPAGDP-DEOXJWBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  66
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  28-O-allyl-oleanate-3-yl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以100%的产率得到28-O-allyl-oleanate-3-yl 2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8
• 作为产物：
  描述：

  3,4,6-三-O-乙酰基-2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 28-O-allyl-oleanate-3-yl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8