2-((3aS,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetic acid | 929875-33-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3aS,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetic acid
• 英文别名: methyl 2-C-(5-azido-5-deoxy-2,3-di-O-isopropylidene-β-D-ribofuranosyl)acetic acid；2-[(3aR,4R,6S,6aS)-4-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]acetic acid
• CAS: 929875-33-2
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: HOQUGGNLLSWGJE-JWIUVKOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((3aS,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetic acid 在 palladium on activated charcoal 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 methyl 2-[[2-[1-[[(3aR,4R,6S,6aS)-6-[2-(2-hydroxyethylamino)-2-oxoethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylamino]-6-(phenylmethoxycarbonylamino)hexyl]-1,3-oxazol-5-yl]-benzylamino]acetate
  参考文献：
  名称：

  通过多组分反应和酸介导的大环化序列快速合成含糖氨基酸或糖氨基醇的环十二肽

  摘要：

  已经合成了掺入糖氨基酸（醇）的环十二肽。糖氨基酸（SAA）衍生物，醛和二肽异腈在回流的甲醇中进行三组分反应，得到相应的5-氨基恶唑，将其皂化后进行三氟乙酸促进的大环化以提供环状糖氨基酸。

  DOI：

  10.1021/jo0621874
• 作为产物：
  描述：

  methyl 3,6-anhydro-7-azido-2,7-dideoxy-4,5-O-isopropylidene-D-allo-heptulonate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以90%的产率得到2-((3aS,6R,6aR)-6-(azidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)acetic acid
  参考文献：
  名称：

  通过还原胺化/酰胺化从C-核糖基叠氮基醛合成呋喃糖-糖氮杂-冠醚的简便方法

  摘要：

  通过一锅还原α-异头异构体C-核糖基叠氮基醛的胺化反应，开发了一种短而高效的途径制备呋喃糖-氮杂-冠冕醚的α-异头物。另外，通过酰胺化由线性二糖前体合成β-端基呋喃糖-氮杂-冠醚，然后进行微波辅助酰胺还原。

  DOI：

  10.1016/j.carres.2009.03.008

文献信息

• [EN] NOVEL HAMAMELITANNIN ANALOGUES AND USES THEREOF<br/>[FR] NOUVEAUX ANALOGUES DU HAMAMÉLITANNIN ET LEURS UTILISATIONS
  申请人：UNIV GENT

  公开号：WO2018065387A1

  公开（公告）日：2018-04-12

  The present invention relates to hamamelitannin analogues, pharmaceutical compositions comprising the same, and combinations thereof with anti-microbial agents such as antibiotics or disinfectants. It in particular relates to the use of the compounds, compositions and combinations according to this invention in human or veterinary medicine, more in particular for use in the prevention and/or treatment of bacterial infections, such as Staphylococcus aureus infections, in humans or animals.

  本发明涉及金缕梅鞣质类似物、包含其的药物组合物，以及与抗微生物药剂（如抗生素或消毒剂）的组合物。特别涉及本发明中的化合物、组合物和组合物在人类或兽医学中的使用，更具体地用于预防和/或治疗细菌感染，如金黄色葡萄球菌感染，在人类或动物身上。
• Convenient approaches to synthesis of furanoid sugar-aza-crown ethers from C-ribosyl azido aldehyde via a reductive amination/amidation
  作者：Yu-Chi Hsieh、Jiun-Ly Chir、Wei Zou、Hsiu-Han Wu、An-Tai Wu

  DOI：10.1016/j.carres.2009.03.008

  日期：2009.5

  alpha-anomer of a furanoid sugar-aza-crown ether was developed by a one-pot reductive amination of an alpha-anomer C-ribosyl azido aldehyde. In addition, the beta-anomer furanoid sugar-aza-crown ether was synthesized from a linear disaccharide precursor via amidation and then followed by microwave-assisted amide reduction.

  通过一锅还原α-异头异构体C-核糖基叠氮基醛的胺化反应，开发了一种短而高效的途径制备呋喃糖-氮杂-冠冕醚的α-异头物。另外，通过酰胺化由线性二糖前体合成β-端基呋喃糖-氮杂-冠醚，然后进行微波辅助酰胺还原。
• A pyrenyl-appended triazole-based ribose as a fluorescent sensor for Hg2+ ion
  作者：Kuan-Hao Chen、Cheng-Yi Lu、Hsiu-Jung Cheng、Shau-Jiun Chen、Ching-Han Hu、An-Tai Wu

  DOI：10.1016/j.carres.2010.09.010

  日期：2010.11

  For the efficient detection of toxic trace metal ions, two pyrenyl-appended triazole-based D-ribose fluorescent chemosensors 6 and 7 were prepared and their fluoroionophoric properties toward transition metal ions were investigated. Chemosensors 6 and 7 exhibit highly selective recognition toward Hg2+ among a series of tested metal ions in CH2Cl2/MeOH solution. The association constants of 6 and 7 are calculated to be 1.73 x 10(5) M-1 and 4.44 x 10(5) M-1, respectively. Both 6 and 7 formed complexes with the Hg2+ ion at a 1:1 ligand-to-metal ratio with a detection limit of 10-15 mu m Hg2+. Computational analysis demonstrated that the Hg2+ ion occupied the coordination center of 6 with N-2 and N-3 atoms in two triazole groups, thus separating and distorting the two parallel pyrenes away from each other. (C) 2010 Elsevier Ltd. All rights reserved.
• Rapid Synthesis of Cyclodepsipeptides Containing a Sugar Amino Acid or a Sugar Amino Alcohol by a Sequence of a Multicomponent Reaction and Acid-Mediated Macrocyclization
  作者：Carine Bughin、Géraldine Masson、Jieping Zhu

  DOI：10.1021/jo0621874

  日期：2007.3.1

  Cyclodepsipeptides incorporating a sugar amino acid (alcohol) have been synthesized. A three-component reaction of a sugar amino acid (SAA) derivative, an aldehyde, and a dipeptide isonitrile in refluxing methanol afforded the corresponding 5-aminooxazole which, after saponification, underwent a trifluoroacetic acid promoted macrocyclization to furnish the cyclic sugar amino acids.

  已经合成了掺入糖氨基酸（醇）的环十二肽。糖氨基酸（SAA）衍生物，醛和二肽异腈在回流的甲醇中进行三组分反应，得到相应的5-氨基恶唑，将其皂化后进行三氟乙酸促进的大环化以提供环状糖氨基酸。