allyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside | 628280-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-ol
• CAS: 628280-91-1
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: BTTNRPDLVFRVJQ-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 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 、 二甲基亚砜 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.25h， 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：

  allyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 methyl orange 盐酸 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 allyl 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

文献信息

• p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification
  作者：Nadine Barroca-Aubry、Mohamed Benchekroun、Filipe Gomes、David Bonnaffé

  DOI：10.1016/j.tetlet.2013.07.066

  日期：2013.9

  PMB-NPTFA la is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)(3). The mild conditions of the reaction confer a good orthogonality to acid- and base-sensitive protecting groups. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.
• 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.
• 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)