methyl 2,3,4-tri-O-acetyl-6-methyl-α-D-glucuronopyranoside | 50767-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-methyl-α-D-glucuronopyranoside
• 英文别名: methyl (methyl tri-O-acetyl-α-D-glucopyranosid)uronate；Methyl-2,3,4-tri-O-acetyl-β-D-glucuronsaeure-methylester；O²,O³,O⁴-triacetyl-O¹-methyl-α-D-glucopyranuronic acid methyl ester；O²,O³,O⁴-Triacetyl-O¹-methyl-α-D-glucopyranuronsaeure-methylester；I+/--D-Glucopyranosiduronic acid, methyl, methyl ester, 2,3,4-triacetate；methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxane-2-carboxylate
• CAS: 50767-72-1
• 化学式: C₁₄H₂₀O₁₀
• 分子量: 348.307
• InChiKey: WQZLHCDEZYULJJ-GCQYFTOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.67
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-methyl-α-D-glucuronopyranoside 在 吡啶 、 甲醇 、 氨 作用下， 生成 O²,O³,O⁴-triacetyl-O¹-methyl-α-D-glucopyranuronic acid amide
  参考文献：
  名称：

  α-甲基-D-葡萄糖醛-吡喃糖苷衍生物的制备

  摘要：

  通过用四氧化二氮氧化α-甲基-葡萄糖-吡喃糖苷，我们首次成功地生产了纯结晶的α-甲基-葡萄糖醛酸-吡喃糖苷衍生物。

  DOI：

  10.1002/hlca.19490320642
• 作为产物：
  描述：

  乙酸酐 、 methyl α-D-glucuronide methyl ester 在 吡啶 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-methyl-α-D-glucuronopyranoside
  参考文献：
  名称：

  α-甲基-D-葡萄糖醛-吡喃糖苷衍生物的制备

  摘要：

  通过用四氧化二氮氧化α-甲基-葡萄糖-吡喃糖苷，我们首次成功地生产了纯结晶的α-甲基-葡萄糖醛酸-吡喃糖苷衍生物。

  DOI：

  10.1002/hlca.19490320642

文献信息

• Studies on the constituents of Momordica cochinchinensis Spreng. II. Isolation and characterization of the root saponins, Momordins I, II and III.
  作者：MASAYO IWAMOTO、HIKARU OKABE、TATSUO YAMAUCHI

  DOI：10.1248/cpb.33.1

  日期：——

  From the root of Momordica cochinchinensis SPRENG. (Cucurbitaceae), three saponins named momordins I, II and III have been isolated. Their structures were determined on the basis of chemical and spectral evidence as oleanolic acid 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin I), 28-O-β-D-glucopyranoside of momordin I (momordin II) and 3β-hydroxy-11α, 12α-epoxy-olean-28, 13-olide 3-O-α-L-arabinopyranosyl (1→3)-β-D-glucuronopyranoside (momordin III). Momordin II was proved to be identical with hemsloside Ma1 isolated from the tubers of Hemsleya macrosperma and H. chinensis.

  从木鳖子（Momordica cochinchinensis SPRENG. 葫芦科）的根中分离出三种皂苷，命名为木鳖子苷I、II和III。它们的结构通过化学和光谱证据确定为：木鳖子苷I（3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷基的齐墩果酸）、木鳖子苷II（木鳖子苷I的28-O-β-D-葡萄糖苷）和木鳖子苷III（3β-羟基-11α, 12α-环氧-齐墩果-28, 13-内酯的3-O-α-L-阿拉伯吡喃糖基（1→3）-β-D-葡萄糖醛酸苷）。木鳖子苷II被证实与从大苞赤瓟和中华赤瓟块根中分离出的hemsloside Ma1相同。
• An efficient and direct esterification of uronic acids using H2SO4-SiO2 at room temperature
  作者：Varsha Tiwari、Kaliyappan Murugan、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1016/j.tetlet.2022.153852

  日期：2022.6

  A simple and convenient method for the esterification of various monosaccharide and disaccharide uronic acids, derived from glucose, galactose and mannose, was developed with different alcohols using the eco-friendly catalyst silica-sulphuric acid (H2SO4-SiO2). The esterification reactions proceeded at room temperature under mild conditions with excellent yields. Under the standard reaction conditions

  使用环保催化剂二氧化硅-硫酸（H 2 SO 4 -SiO 2），开发了一种简便的酯化方法，用于由葡萄糖、半乳糖和甘露糖衍生的各种单糖和二糖糖醛酸与不同醇的酯化反应。酯化反应在室温下温和条件下以优异的产率进行。在标准反应条件下，对乙酰基、苯甲酰基、新戊酰基、异亚丙基、苄基、萘基等各种敏感保护基团具有良好的耐受性。部分保护的糖醛酸在不发生自缩合反应的情况下进行酯化。
• Efficient glycosydation and/or esterification of d-glucuronic acid and its 6,1-lactone under solvent-free microwave irradiation
  作者：Stéphanie Rat、David Mathiron、Philippe Michaud、José Kovensky、Anne Wadouachi

  DOI：10.1016/j.tet.2007.09.043

  日期：2007.12

  2,3,4-Tri-O-acetyl-D-glucurono-6,1-lactone was obtained 'one-pot' from D-glucuronic acid. The lactone opening with different alcohols in the presence of a variety of catalysts was studied. All reactions were performed under microwave irradiatio in solvent-free conditions. (c) 2007 Elsevier Ltd. All rights reserved.