cholesteryl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside | 115533-30-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside
• CAS: 115533-30-7
• 化学式: C₄₆H₆₇NO₁₀
• 分子量: 794.039
• InChiKey: KLACMDCSDMJGPO-VRQMWIHRSA-N

物化性质

• 沸点：
  766.2±60.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  57.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  cholesteryl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (2R,3R,4S,5R,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl phenylcarbamate
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-5,6-diacetoxy-2-acetoxymethyl-4-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester 在 氢溴酸 、 Silber-4-hydroxy-valerat 、 溶剂黄146 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 11.5h， 生成 cholesteryl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5