olean-12-en-28-oic acid 3-hydroxymethyl-β-D-glucopyranuronosyl ester | 697795-92-9

• 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: olean-12-en-28-oic acid 3-hydroxymethyl-β-D-glucopyranuronosyl ester
• CAS: 697795-92-9
• 化学式: C₃₇H₅₈O₉
• 分子量: 646.862
• InChiKey: XIOBUTFJBOVLFI-YICSIWRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  46.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  142.75
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  olean-12-en-28-oic acid 3-hydroxymethyl-β-D-glucopyranuronosyl ester 在 水 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (2S,3S,4S,5R,6S)-6-[(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents

  摘要：

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.019
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 olean-12-en-28-oic acid 3-hydroxymethyl-β-D-glucopyranuronosyl ester
  参考文献：
  名称：

  Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents

  摘要：

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.019

文献信息

• Synthesis of Bisdesmosidic Oleanolic Acid Saponins via a Glycosylation-Deprotection Sequence under Continuous Microfluidic/Batch Conditions
  作者：Naruki Konishi、Tatsuya Shirahata、Masaki Yokoyama、Tatsuya Katsumi、Yoshikazu Ito、Nozomu Hirata、Takashi Nishino、Kazuishi Makino、Noriko Sato、Takayuki Nagai、Hiroaki Kiyohara、Haruki Yamada、Eisuke Kaji、Yoshinori Kobayashi

  DOI：10.1021/acs.joc.7b00841

  日期：2017.7.7

  a series of bisdesmosidic oleanolic acid saponins using microflow reactor Comet X-01 via a continuous flow glycosylation-batch deprotection sequence. The main results of this study can be summarized as follows: (1) The microfluidic glycosylation of oleanolic acid at C-28 was achieved in quantitative yield and was applied to the synthesis of six C-28-monoglycosidic saponins. (2) The microfluidic glycosylation

  我们报告了通过连续流动糖基化-分批脱保护序列，使用微流反应器Comet X-01合成了一系列双去甲齐墩果油酸皂苷的首次合成。这项研究的主要结果可以概括如下：（1）以定量产率实现了齐墩果酸在C-28上的微流体糖基化，并被用于合成6种C-28-单糖苷皂苷。（2）在不产生原酸酯副产物的情况下，以良好的产率实现了齐墩果酸在C-3的微流体糖基化，并被用于合成三种双去糖苷皂苷。（3）通过涉及两个纯化的四个步骤，通过微流体糖基化-分批脱保护序列来连续合成皂苷。因此，
• A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)2 under aqueous conditions
  作者：Feng Lin、Wenjie Peng、Wen Xu、Xiuwen Han、Biao Yu

  DOI：10.1016/j.carres.2004.02.001

  日期：2004.4

  the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.

  在TEMPO介导的选择性氧化中添加固体Ca（OCl）（2）作为终端氧化剂具有易于操作的优点。多种部分受保护的糖衍生物（1a-1）已成功转化为相应的尿酸酯衍生物，包括GAG片段的二糖结构单元和皂苷的前体。在某些底物的氧化中也公开了Aliquat 336的有益作用。