6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid | 668990-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid
• 英文别名: (4R,5S)-5-[(4S,5R)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 668990-26-9
• 化学式: C₁₂H₁₉N₃O₆
• 分子量: 301.299
• InChiKey: NLRNBWHZBVCPCT-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid 在 sodium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-{[(4S,5R,4'S,5'R)-5'-({6-[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-hexanoylamino}-methyl)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl]-amino}-hexanoic acid methyl ester
  参考文献：
  名称：

  混合糖–尼龙14、28和42元环大环内酰胺

  摘要：

  从6-氨基-6-脱氧-d-半乳糖酸（或6-氨基-6-脱氧-d-甘露酸）和6-氨基己酸的混合低聚物中氢化线性ω-叠氮基-五氟苯基酯，得到的环肽为14 -，28-和42-元环内酰胺。衍生自ε-氨基酸的四聚体肽的氢化反应产生28元环内酰胺，产率为79％。

  DOI：

  10.1016/j.tetlet.2003.10.105
• 作为产物：
  描述：

  methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 在 水 、 barium(II) hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid
  参考文献：
  名称：

  6-氨基-6-脱氧半乳糖酸和苯丙氨酸的多相环状低聚物的合成与构象分析

  摘要：

  非常感谢根据合同 HPRN-CT-2002-00173 通过欧洲共同体的人类潜力计划为 RS 提供的财政支持。

  DOI：

  10.1002/ejoc.201200463

文献信息

• Synthesis and Conformational Analysis of Heterogeneous Cyclic Oligomers of 6-Amino-6-deoxygalactonic Acid and Phenylalanine
  作者：Raquel G. Soengas、Marco Fontanella、Jose I. Santos、George W. J. Fleet、Jesús Jiménez-Barbero

  DOI：10.1002/ejoc.201200463

  日期：2012.10

  Financial support to R. S. provided through the European Community's Human Potential Programme under contract HPRN-CT-2002-00173 is gratefully acknowledged.

  非常感谢根据合同 HPRN-CT-2002-00173 通过欧洲共同体的人类潜力计划为 RS 提供的财政支持。
• Towards hydroxylated nylon 6: linear and cyclic oligomers from a protected 6-amino-6-deoxy-d-galactonate––a novel class of carbopeptoid-cyclodextrin (CPCD)
  作者：Benjamin A. Mayes、Rebecca J.E. Stetz、Mark P. Watterson、Alison A. Edwards、Christopher W.G. Ansell、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tetasy.2003.12.031

  日期：2004.2

  Circular dichroism studies on a series of linear oligomers derived from a protected 6-amino-6-deoxy-D-galactonate (an epsilon-amino acid) indicated a predisposition to form a rigid structure in solution, which is comparable to a beta-sheet composed Of L-amino acids; in contrast, a diastereomeric allonate series provided no evidence for secondary structure. A linear tetramer was cyclised to a 28-membered ring lactam in modest yield, which on deprotection formed a class of macrocycle with structural features of both a cyclic peptide and a cyclodextrin. (C) 2004 Elsevier Ltd. All rights reserved.
• Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin
  作者：Benjamin A. Mayes、Rebecca J.E. Stetz、Christopher W.G. Ansell、George W.J. Fleet

  DOI：10.1016/j.tetlet.2003.10.104

  日期：2004.1

  The formation of the 28-membered ring cyclo[(6-amino-6-deoxy-D-galactonic acid)(4)] by cyclisation of a protected open chain fully hydroxylated nylon 6 linear tetramer in modest yield provides the first example of a new class of carbopeptoid-cyclodextrin. (C) 2003 Elsevier Ltd. All rights reserved.
• [EN] METHOD FOR DETECTING AN ANALYTE OF INTEREST IN A SAMPLE<br/>[FR] PROCÉDÉ DE DÉTECTION D'UN ANALYTE D'INTÉRÊT DANS UN ÉCHANTILLON
  申请人：[en]F. HOFFMANN-LA ROCHE AG

  公开号：WO2022136234A1

  公开（公告）日：2022-06-30

  The present invention relates to a method for determining at least one analyte of interest. The present invention further relates to a kit, a complex, a method to synthesize a complex and the use thereof for detecting the analyte of interest in the sample.
• Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from <scp>d</scp>-galactose
  作者：M. Verónica Rivas、Gabriela Petroselli、Rosa Erra-Balsells、Oscar Varela、Adriana A. Kolender

  DOI：10.1039/c9ra00398c

  日期：——

  proportions of cyclic oligomer byproducts were detected. The Cu-catalyzed click polymerization led regioselectively to 1,4-disubstituted triazole linkages, while the thermal, metal-free polymerization produced a random distribution of 1,4- and 1,5-disubstituted triazoles in the polymer backbone. The poly(ester-triazole)s exhibited high molecular weights (Mw in the range 35–85 kDa). They were soluble in

  设计和合成α-叠氮化物-ω-炔基酯单体以获得可水解降解的聚合物。单体是由作为可再生资源的D-半乳糖制备的。进行环境友好的叠氮基-炔烃环加成聚合，得到具有完全原子经济性的聚（酯-三唑）。尽管在优化的聚合条件下聚合物形成占优势，但检测到不同比例的环状低聚物副产物。Cu催化的点击聚合区域选择性地产生1,4-二取代三唑键，而热、无金属聚合在聚合物主链中产生1,4-和1,5-二取代三唑的随机分布。聚（酯-三唑）表现出高分子量（M w在 35-85 kDa 范围内）。它们可溶于有机溶剂，但高度不溶于水，因此简化了 Cu( I ) 催化剂的去除。聚合物在高达 300 °C 时保持稳定，并且T g值在 90–100 °C 范围内。材料在碱性或强酸条件下水解，降解产物已被表征。