hexadeca-O-methyl-2,3-di-O-galloyl-4,6-(S)-valoneoyl-α-D-glucose | 126347-62-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: hexadeca-O-methyl-2,3-di-O-galloyl-4,6-(S)-valoneoyl-α-D-glucose
• 英文别名: methyl 2-[[(10R,11S,12R,13S,15R)-3,4,13,21,22,23-hexamethoxy-8,18-dioxo-11,12-bis[(3,4,5-trimethoxybenzoyl)oxy]-9,14,17-trioxatetracyclo[17.4.0.02,7.010,15]tricosa-1(23),2,4,6,19,21-hexaen-5-yl]oxy]-3,4,5-trimethoxybenzoate
• CAS: 126347-62-4
• 化学式: C₅₇H₆₂O₂₇
• 分子量: 1179.1
• InChiKey: PXESMEVZCGYOCK-OJXXDLBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  84
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  288
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 54.5h， 生成 hexadeca-O-methyl-2,3-di-O-galloyl-4,6-(S)-valoneoyl-α-D-glucose
  参考文献：
  名称：

  Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B

  摘要：

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.004

文献信息

• Camelliin B and nobotanin I, macrocyclic ellagitannin dimers and kelated dimers, and their antitumor activity.
  作者：Takashi YOSHIDA、Tong CHOU、Kumiko HABA、Yoshiaki OKANO、Tetsuro SHINGU、Ken-ici MIYAMOTO、Ryozo KOSHIURA、Takuo OKUDA

  DOI：10.1248/cpb.37.3174

  日期：——

  Camelliin B and nobotanin I, dimeric hydrolyzable tannins of a new class having macrocyclic structures, were isolated from Camellia japonica and Heterocentron roseum, respectively. Nobotanin G and H of the structures related to nobotanin I, were also obtained from H. roseum. Camelliin B and also woodfordin C, a macrocyclic dimer from Woodfordia fruticosa, exhibited marked host-mediated antitumor activities

  分别从山茶和蔷薇杂种中分离出具有大环结构的新型二聚体可水解单宁酸茶黄素B和NobotaninI。也从玫瑰色的H.roseum获得了与Nobotanin I有关的结构的Nobotanin G和H。茶花素B和木香素C（一种来自金木参的大环二聚体）表现出明显的宿主介导的抗肿瘤活性。
• Synthesis of All-Methylated Isorugosin B
  作者：Kazuma Shioe、Yasuo Takeuchi、Takashi Harayama、Hitoshi Abe

  DOI：10.1248/cpb.58.435

  日期：——

  All-methylated isorugosin B was synthesized via two-step esterification between optically active valoneic acid and glucose derivatives.

  全甲基化异龙胆素 B 是通过光学活性丙酮酸和葡萄糖衍生物之间的两步酯化反应合成的。
• Tannins of theaceous plants. II. Camelliins A and B, two new dimeric hydrolyzable tannins from flower buds of Camellia japonica L. and Camellia sasanqua Thunb.
  作者：Takashi YOSHIDA、Tong CHOU、Yasuhiko MARUYAMA、Takuo OKUDA

  DOI：10.1248/cpb.38.2681

  日期：——

  Two new dimeric hydrolyzable tannins, camelliins A and B, which exist as equilibrium mixtures of anomers, have been isolated from flower buds of Camellia japonica L., and their structures were elucidated. Camelliin B belongs to a unique class of dimers having a macrocyclic structure. The flower of Camellia sasanqua THUNB. yielded five tannins which were identical with those of C. japonica.

  从山茶花的花蕾中分离出两种新的二聚可水解单宁，即山茶素A和B，它们以平衡混合物形式存在于异构体中，其结构已得到阐明。山茶素B属于具有大环结构的独特二聚体。山茶花（Camellia sasanqua THUNB.）的花中提取出五种单宁，与山茶花（C. japonica）的单宁完全相同。
• Syntheses of all-methylated ellagitannin, isorugosin B and rugosin B
  作者：Kazuma Shioe、Yusuke Sahara、Yoshikazu Horino、Takashi Harayama、Yasuo Takeuchi、Hitoshi Abe

  DOI：10.1016/j.tet.2011.01.004

  日期：2011.3

  Ellagitannins possess a wide range of biological activities and remarkable structural diversity, which commonly include an axially chiral biaryl unit. This paper describes syntheses of all-methylated versions of isorugosin B and rugosin B, which are regioisomeric, ellagitannin-related compounds. The key features of these syntheses involve the construction of an axially chiral biaryl function on a sugar moiety through a Pd-catalyzed intramolecular biaryl coupling reaction, Bringmann's atroposelective lactone opening reaction, and a two-step ester formation. This is the first synthetic approach for generating ellagitannins featuring a valoneoyl group. (C) 2011 Elsevier Ltd. All rights reserved.