(2S,3R,4R,5S,6S)-2-(((3aS,6S,7R,7aS)-6-(allyloxy)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 616201-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6S)-2-(((3aS,6S,7R,7aS)-6-(allyloxy)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• 英文别名: [(2S,3S,4R,5R,6S)-6-[[(3aS,6S,7R,7aS)-2,2-dimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate
• CAS: 616201-13-9
• 化学式: C₃₈H₄₀O₁₂
• 分子量: 688.728
• InChiKey: GYSDKAPZKIYBGL-ZYDRYLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6S)-2-(((3aS,6S,7R,7aS)-6-(allyloxy)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 palladium dichloride 吡啶 、 四丁基溴化铵 、 氢溴酸 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 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：

  allyl 3,4-O-isopropylidene-β-L-arabinopyranoside 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2S,3R,4R,5S,6S)-2-(((3aS,6S,7R,7aS)-6-(allyloxy)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  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

文献信息

• Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C₆F₅)₃-catalyzed glycosylation of sterically-hindered precursors
  作者：Rashad R. Karimov、Derek S. Tan、David Y. Gin

  DOI：10.1039/c7cc01783a

  日期：——

  natural-product immunoadjuvant jujuboside A is described. The key step is a sterically-hindered glycosylation reaction between a branched trisaccharide trichloroacetimidate glycosyl donor and a disaccharide glycosyl acceptor. Conventional Lewis acids (TMSOTf, BF3·Et2O) were ineffective in this glycosylation, but B(C6F5)3 catalyzed the reaction successfully. Inherent complete diastereoselectivity for

  描述了天然产物免疫佐剂大枣糖苷A的复杂的双分支五糖结构域的会聚合成。关键步骤是支链三糖三氯乙酰亚胺酸酯糖基供体和二糖糖基受体之间的空间受阻的糖基化反应。常规路易斯酸（TMSOTf，BF 3 ·Et 2 O）在这种糖基化反应中无效，但是B（C 6 F 5）3成功地催化了该反应。通过使用腈溶剂系统（1 ：5 t -BuCN / CF 3Ph），以灵活，有效地获取β-连接的五糖。
• The first total synthesis of calabricoside A
  作者：Yuguo Du、Guohua Wei、Robert J. Linhardt

  DOI：10.1016/s0040-4039(03)01706-4

  日期：2003.9

  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.