4-Nitro-benzoic acid (3R,4S,5S)-4,5-diacetoxy-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzoyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester | 616201-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Nitro-benzoic acid (3R,4S,5S)-4,5-diacetoxy-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzoyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester
• 英文别名: [(3R,4S,5S)-4,5-diacetyloxy-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-2-yl] 4-nitrobenzoate
• CAS: 616201-17-3
• 化学式: C₄₃H₃₉NO₁₇
• 分子量: 841.779
• InChiKey: ROZKZELLGMOHNO-BVKUZVDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  61
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  231
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-Nitro-benzoic acid (3R,4S,5S)-4,5-diacetoxy-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzoyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester 在 吡啶 、 四丁基溴化铵 、 氢溴酸 、 potassium carbonate 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 [(2S,3S,4R,5R,6S)-4,5-dibenzoyloxy-6-[(2S,3R,4S,5S)-4,5-diacetyloxy-2-[5-acetyloxy-2-[3-acetyloxy-4-[(4-methoxyphenyl)methoxy]phenyl]-7-[(4-methoxyphenyl)methoxy]-4-oxochromen-3-yl]oxyoxan-3-yl]oxy-2-methyloxan-3-yl] benzoate
  参考文献：
  名称：

  The first total synthesis of calabricoside A

  摘要：

  Quercetin 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (calabricoside A), a new flavonol triglycoside isolated from the aerial parts of Putoria calabrica showing strong radical scavenging activity, was synthesized through a combination of phase-transfer-catalyzed C-3 glycosylation and AgOTf promoted homogeneous C-7 glycosylation in CH2Cl2. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01706-4
• 作为产物：
  描述：

  (2S,3R,4R,5S,6S)-2-(((2S,3R,4S,5S)-4,5-diacetoxy-2-(allyloxy)tetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 palladium dichloride 吡啶 、 sodium acetate 、 溶剂黄146 作用下， 生成 4-Nitro-benzoic acid (3R,4S,5S)-4,5-diacetoxy-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzoyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  The first total synthesis of calabricoside A

  摘要：

  Quercetin 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (calabricoside A), a new flavonol triglycoside isolated from the aerial parts of Putoria calabrica showing strong radical scavenging activity, was synthesized through a combination of phase-transfer-catalyzed C-3 glycosylation and AgOTf promoted homogeneous C-7 glycosylation in CH2Cl2. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01706-4