allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 628280-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• 英文别名: (2R,4aR,6S,7R,8R,8aS)-7-azido-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 628280-97-7
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: WOGBACPARLUOOY-SJJUBHFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 methyl orange 盐酸 、 三乙基硅烷 、 氢氧化钾 、 草酰氯 、 camphor-10-sulfonic acid 、 二氯苯酚溴酯 、 碘 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-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
• 作为产物：
  描述：

  (3aR,4S,6R,7S,7aR)-3-acetyl-7-hydroxy-6-(phenylmethoxymethyl)-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one 在 吡啶 、 triflic azide 、 copper(II) sulfate 、 三乙胺 作用下， 生成 allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments

  摘要：

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.124

文献信息

• 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。
• [EN] SILVER ASSISTED GOLD CATALYSIS FOR THE PREPARATION OF FONDAPARINUX PENTASACCHARIDE AND INTERMEDIATES<br/>[FR] CATALYSE À L'OR ASSISTÉE PAR L'ARGENT POUR LA PRÉPARATION DE PENTASACCHARIDE DE FONDAPARINUX ET D'INTERMÉDIAIRES
  申请人：INDIAN INSTITUTE OF SCIENCE EDUCATION AND RES

  公开号：WO2022107013A1

  公开（公告）日：2022-05-27

  The present invention relates to a process for the synthesis of Fondaparinux pentasaccharide and its intermediates. Specifically, the present invention relates to a novel catalytic process for the synthesis of Fondaparinux pentasaccharide and its intermediates. The present invention further relates to a silver assisted gold catalysis for glycosylation reactions in the synthesis of Fondaparinux pentasaccharide and its intermediates. (I)

  本发明涉及一种合成Fondaparinux五糖及其中间体的过程。具体而言，本发明涉及一种新型催化合成Fondaparinux五糖及其中间体的过程。本发明还涉及在合成Fondaparinux五糖及其中间体的糖基化反应中使用银辅助金催化的方法。
• 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)
• Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments
  作者：Luigi Cirillo、Emiliano Bedini、Antonio Molinaro、Michelangelo Parrilli

  DOI：10.1016/j.tetlet.2009.12.124

  日期：2010.2

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.