methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate | 87327-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate
• 英文别名: methyl 2,4-di-O-acetyl-3-O-benzyl-L-idofuranuronyl bromide；methyl (2R,3S,4S,5R,6S)-3,5-diacetyloxy-6-bromo-4-phenylmethoxyoxane-2-carboxylate
• CAS: 87327-03-5
• 化学式: C₁₈H₂₁BrO₈
• 分子量: 445.264
• InChiKey: VUJSCPJFKRFXDQ-FIDHJVLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate 生成 methyl (2S,3aR,5R,6S,7S,7aR)-6-acetyloxy-2-methoxy-2-methyl-7-phenylmethoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-carboxylate
  参考文献：
  名称：

  CHOAY, J.;JACQUINET, J. -C.;PETITOU, M.;SINAY, P.

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate 在 溴化钛(IV) 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 以96%的产率得到methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate
  参考文献：
  名称：

  肝素片段的合成。三糖O-（2-脱氧-2-磺酰胺基-3,6-二-O-磺基-α-d-吡喃葡萄糖基）-（1→4）-O-（2-O-磺基-α的化学合成-l-idopyranosyluronic acid）-（1→4）-2-deoxy-2-sulfamido-6-O-sulfo-d-pyramypyranose heptasodium salt

  摘要：

  摘要首先将已知的3-O-苄基-1,2-O-异亚丙基-α-d-葡萄糖基呋喃糖转化为3-O-苄基-1,2-O-异亚丙基-β-1-基呋喃醛酸甲酯。酸水解，然后乙酰化并用四溴化钛处理，得到（2,4-二-O-乙酰基-3-O-苄基-α-1-吡喃吡喃基溴化）甲基脲酸酯，其立即被转化为4-O-甲基。乙酰基-3-O-苄基-β-1-氨基吡喃二酸酯1,2-（原乙酸叔丁酯）。用4-O-氯乙酰基进行两步取代4-O-乙酰基得到关键的衍生物结晶结晶3-O-苄基-4-O-氯乙酰基-β-1-氨基吡喃醛酸酯1,2-（叔-原乙酸正丁酯）。该原酸酯与过量的苄基6-O-乙酰基-3-O-苄基-2-（苄氧基羰基）氨基-2-脱氧-α-d-吡喃葡萄糖苷结晶在氯苯存在下缩合2，6-二甲基吡啶鎓高氯酸盐得到结晶的苄基6-O-乙酰基-3-O-苄基-2-（苄氧基羰基）氨基-2-脱氧-4-O-（甲基2-O-乙酰基-3-O-苄基-4- O-氯乙酰基-

  DOI：

  10.1016/0008-6215(84)85281-7

文献信息

• Efficient Preparation of Three Building Blocks for the Synthesis of Heparan Sulfate Fragments: Towards the Combinatorial Synthesis of Oligosaccharides from Hypervariable Regions
  作者：Ollivier Gavard、Yaël Hersant、Jocelyne Alais、Véronique Duverger、Anna Dilhas、Alison Bascou、David Bonnaffé

  DOI：10.1002/ejoc.200300254

  日期：2003.9

  described. The L-iduronyl and D-glucuronyl disaccharides 1−3 were then prepared from these compounds, by means of efficient and regioselective protective group manipulations. These disaccharides form the basis of a combinatorial approach toward the synthesis of heparan sulfate fragments representative of the heterogeneous regions of this polysaccharide. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  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)
• Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same
  申请人：Bonnaffe David

  公开号：US20060166927A1

  公开（公告）日：2006-07-27

  Compound capable of binding to gamma-interferon (γ-IFN), chosen from the molecules corresponding to formula (I) below: in which X is a divalent spacer group that is sufficiently long to allow the two oligosaccharide fragments A and B to each bind to one of the peptide sequences 125 to 143 of the C-terminal ends of a γ-interferon (γ-IFN) homodimer, n represents an integer from 0 to 10, and for example equal to 0, 1, 2, 3, 4 or 5, and each R independently represents a hydrogen atom, an SO 3 − group or a phosphate group, on the condition that no SO 3 − group is in the 3-position of the glucosamine units of compound (I). The invention also relates to the process for preparing these compounds, to the complexes formed by these compounds and gamma-interferon, and to the medicaments comprising these compounds or complexes.

  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。
• 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.