allyl [methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside | 628280-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl [methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: Allyl (methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-alpha-L-idopyranosyluronate)-(1,4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-alpha-D-glucopyranoside；methyl (2R,3S,4S,5R,6R)-5-acetyloxy-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-5-azido-4-phenylmethoxy-6-prop-2-enoxyoxan-3-yl]oxy-3-[(4-methoxyphenyl)methoxy]-4-phenylmethoxyoxane-2-carboxylate
• CAS: 628280-86-4
• 化学式: C₄₂H₄₉N₃O₁₄
• 分子量: 819.863
• InChiKey: GIXVFRMPNQYUCW-HWNLGKFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  allyl [methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到allyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same

  摘要：

  能够与干扰素-γ（γ-IFN）结合的化合物，选自符合以下公式（I）的分子：其中X是一个二价间隔基团，足够长以允许两个寡糖片段A和B各自结合到一个γ-干扰素（γ-IFN）同源二聚体的C端末端的肽序列125至143，n代表从0到10的整数，例如等于0、1、2、3、4或5，并且每个R独立代表一个氢原子、一个SO3−基团或一个磷酸基团，条件是在化合物（I）的葡萄糖胺单元的3位上没有SO3−基团。本发明还涉及制备这些化合物的方法，这些化合物与干扰素-γ形成的复合物，以及包含这些化合物或复合物的药物。

  公开号：

  US20060166927A1
• 作为产物：
  描述：

  allyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 Dowex 50X₈ 200 H(+) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 allyl [methyl 2-O-acetyl-3-O-benzyl-4-O-(4-methoxybenzyl)-α-L-idopyranosyluronate]-(1->4)-O-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  用于合成硫酸乙酰肝素片段的三种构件的有效制备：走向高变区低聚糖的组合合成

  摘要：

  描述了获得适当保护的 L-艾杜糖醛酸单糖供体 4 和 5 以及 2-叠氮葡萄糖受体 6 和 7 的新的多克路线。然后通过有效和区域选择性的保护基操作，从这些化合物制备 L-艾杜糖醛酸和 D-葡萄糖醛酸二糖 1-3。这些二糖构成了合成代表这种多糖异质区域的硫酸乙酰肝素片段的组合方法的基础。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300254

文献信息

• Repairing the Thiol-Ene Coupling Reaction
  作者：Guillaume Povie、Anh-Tuan Tran、David Bonnaffé、Jacqueline Habegger、Zhaoyu Hu、Christine Le Narvor、Philippe Renaud

  DOI：10.1002/anie.201309984

  日期：2014.4.7

  AbstractThiol‐ene coupling (TEC) reactions emerged as one of the most useful processes for coupling different molecular units under reaction mild conditions. However, TEC reactions involving weak CH bonds (allylic and benzylic fragments) are difficult to run and often low yielding. Mechanistic studies demonstrate that hydrogen‐atom transfer processes at allylic and benzylic positions are responsible for the lack of efficiency of the radical‐chain process. These competing reactions cannot be prevented, but reported herein is a method to repair the chain process by running the reaction in the presence of triethylborane and catechol. Under these reaction conditions, a unique repair mechanism leads to an efficient chain reaction, which is demonstrated with a broad range of anomeric O‐allyl sugar derivatives including mono‐, di‐, and tetrasaccharides bearing various functionalities and protecting groups.
• PhBCl2 promoted reductive opening of 2′,4′-O-p-methoxybenzylidene: new regioselective differentiation of position 2′ and 4′ of α-l-iduronyl moieties in disaccharide building blocks
  作者：Anna Dilhas、David Bonnaffé

  DOI：10.1016/j.tetlet.2004.03.046

  日期：2004.4

  We describe a new protocol for the challenging differentiation of the position 2' and 4' of L-iduronyl moieties located at the nonreducing end of various disaccharide building blocks. This methodology is based on the introduction of a 2',4'-O-p-methoxybenzylidene group, followed by a totally regioselective reductive opening of this acetal by the PhBCl2/Et3SiH reagent system, L-Iduronyl moieties protected by a 4'-O-p-methoxybenzyl group were thus obtained regioselectively and efficiently. (C) 2004 Elsevier Ltd. All rights reserved.