4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside | 1004771-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-Diacetyloxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-3-yl] acetate
• CAS: 1004771-43-0
• 化学式: C₁₉H₂₄O₁₀
• 分子量: 412.394
• InChiKey: GHLFYLRACWRIOZ-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 、 ethyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到4-methoxyphenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  从民间药中分离出二倍体三萜皂苷类黄素总皂苷II的合成狄武，Di Wu

  摘要：

  总黄酮苷II，3-O-α-L-鼠李吡喃糖基-（1-> 2）-β-D-吡喃并吡喃基果酸28-O-α-L-鼠李吡喃糖基-（1-> 4）-β -D-吡喃葡萄糖基-（1-> 6）-β-D-吡喃葡萄糖苷是从异丙基2-O-乙酰基-3,4-二-O-苯甲酰基-的结构单元中分离而来的1-硫代-β-D-吡喃吡喃糖苷，2,3,4-三-O-苯甲酰基-α-L-鼠李吡喃糖基三氯乙酰亚胺酸酯，齐墩果酸三苯甲基酯，2,3-二-O-乙酰基-6-O-苯甲酰基乙酯-1-硫代-β-D-吡喃葡萄糖苷和4-甲氧基苯基2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷。使用部分保护的硫糖基供体可大大简化目标皂苷的合成。

  DOI：

  10.1016/j.carres.2007.11.015
• 作为产物：
  描述：

  4-甲氧苯基-2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 二氯二茂锆 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以51%的产率得到4-methoxyphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  区分用于烷基化和芳基化反应的锍叶立德的非叶立基碳硫键断裂

  摘要：

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。

  DOI：

  10.1016/j.cclet.2021.06.069

文献信息

• Synthesis of Calocybe indica var. APK2 polysaccharide repeating unit
  作者：Lei Zhang、Xiangming Zhu

  DOI：10.1016/j.carres.2014.04.004

  日期：2014.6

  The first total synthesis of p-methoxyphenyl alpha-L-fucopyranosyl-(1 -> 6)-alpha-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (2) was achieved starting from five monosaccharide building blocks. This structure represents the repeating unit of the polysaccharide isolated from edible mushroom Calocybe indica var. APK2, and was synthesized in high overall yield via a convergent '3+ 2' glycosylation strategy. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu
  作者：Xing Huang、Shuihong Cheng、Yuguo Du、Feihong Bing

  DOI：10.1016/j.carres.2009.04.005

  日期：2009.7

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.