β-D-galactopyranosyl oleanolate

• 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: β-D-galactopyranosyl oleanolate
• 英文别名: olean-12-en-28-oic acid 3-hydroxy-β-D-galactopyranosyloxy ester；oleanolic acid 28-O-[β-D-galactopyranosyl] ester；[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (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-carboxylate
• 化学式: C₃₆H₅₈O₈
• 分子量: 618.852
• InChiKey: KMKFOIBUKYMVRJ-CZVPAOHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  齐墩果酸 在 甲醇 、 水 、 甲基三辛基氯化铵 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 β-D-galactopyranosyl oleanolate
  参考文献：
  名称：

  在相转移条件下酸的糖基化。皂苷的部分合成

  摘要：

  通过各种羧酸与乙酰溴糖的反应，可以高产率制备β-D-糖基酯。反应在相转移条件下使用碳酸钾。脱乙酰基得到β-D-糖基羧酸盐。

  DOI：

  10.1016/0040-4039(94)88088-3

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，
• Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides
  作者：Yu Sha、Mao-Cai Yan、Jiao Liu、Yang Liu、Mao-Sheng Cheng

  DOI：10.3390/molecules13071472

  日期：——

  condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new

  齐墩果酸及其苷类是重要的天然产物，具有多种有吸引力的生物活性，如抗肿瘤、抗病毒和抗炎特性。在目前的工作中，15 种带有各种糖基的齐墩果酸皂苷，包括 3-单糖苷、28-单糖苷和 3,28-二糖苷，很容易以高产率合成。选择苄基作为 COOH(28) 基团的保护基团，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。发现碱促进羧酸与溴糖苷的缩合在 28-糖苷的合成中更有效。研究了两种方法并证明在制备 3,28-二糖苷中是可行的。
• Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents
  作者：Jun-Feng Li、Song-Jie Chen、Yu Zhao、Jian-Xin Li

  DOI：10.1016/j.carres.2009.01.019

  日期：2009.3

  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.
• Glycosylation of acids under phase transfer conditions. Partial synthesis of saponins
  作者：Christophe Bliard、Georges Massiot、Serge Nazabadioko

  DOI：10.1016/0040-4039(94)88088-3

  日期：1994.8

  β-D-glycosyl esters are prepared in high yields by reaction of various carboxylic acids and acetobromosugars. The reaction uses potassium carbonate under phase tranfer conditions. Deacetylation affords the β-D-glycosyl carboxylates.

  通过各种羧酸与乙酰溴糖的反应，可以高产率制备β-D-糖基酯。反应在相转移条件下使用碳酸钾。脱乙酰基得到β-D-糖基羧酸盐。