methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate | 229643-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate
• 英文别名: methyl (4R,5S)-5-[(4S,5R)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 229643-36-1
• 化学式: C₁₃H₂₁N₃O₆
• 分子量: 315.326
• InChiKey: IZQOGZZLWURYRE-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 在 水 、 三氟乙酸 作用下， 反应 3.0h， 以91%的产率得到6-azido-6-deoxy-D-galactono-1,4-lactone
  参考文献：
  名称：

  Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids

  摘要：

  在丙酮中，在二甲氧基丙烷和托西酸的作用下，D-半乳糖酸-1,4-内酯可分别生成20%和78%的甲基2,3:5,6-二-O-异亚丙基-D-半乳糖酸酯6（仅C-4上的次羟基未受保护）和甲基2,3:4,5-二-O-异亚丙基-D-半乳糖酸酯5（仅C-6上的主羟基未受保护）。1,4-二脱氧-1,4-亚氨基-D-葡萄糖醇16（一种吡咯烷）的合成以及6-叠氮-6-脱氧-D-半乳糖酸-1,4-内酯22的高效制备都说明了这种易得中间体的价值。将22转化为七元半乳糖内酰胺21（一种四羟基己内酰胺）可得到羟基化尼龙聚合物。半乳糖内酰胺21对多种糖苷酶没有明显的抑制作用。22与三氟甲磺酸酐反应可生成两种外消旋5-（叠氮甲基）四氢呋喃-2-羧酸酯，它们可作为两种系列碳青霉烯类药物的起始原料

  DOI：

  10.1039/a809807g
• 作为产物：
  描述：

  methyl 6-bromo-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate
  参考文献：
  名称：

  d-半乳糖衍生的聚（酯-三唑）的合成、表征和化学降解†

  摘要：

  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。

  DOI：

  10.1039/c9ra00398c

文献信息

• Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids
  作者：Daniel D. Long、Rebecca J. E. Stetz、Robert J. Nash、Daniel G. Marquess、Janet D. Lloyd、Ana L. Winters、Naoki Asano、George W. J. Fleet

  DOI：10.1039/a809807g

  日期：——

  Treatment of D-galactono-1,4-lactone with dimethoxypropane in acetone in the presence of tosic acid forms methyl 2,3:5,6-di-O-isopropylidene-D-galactonate 6 (with only the secondary hydroxy group at C-4 unprotected) and methyl 2,3:4,5-di-O-isopropylidene-D-galactonate 5 (with only the primary hydroxy group at C-6 unprotected) in yields of 20% and 78%, respectively. The value of such easily accessible intermediates is illustrated by the synthesis of 1,4-dideoxy-1,4-imino-D-glucitol 16 (a pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono-1,4-lactone 22. The conversion of 22 to a seven-membered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2-carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn.

  在丙酮中，在二甲氧基丙烷和托西酸的作用下，D-半乳糖酸-1,4-内酯可分别生成20%和78%的甲基2,3:5,6-二-O-异亚丙基-D-半乳糖酸酯6（仅C-4上的次羟基未受保护）和甲基2,3:4,5-二-O-异亚丙基-D-半乳糖酸酯5（仅C-6上的主羟基未受保护）。1,4-二脱氧-1,4-亚氨基-D-葡萄糖醇16（一种吡咯烷）的合成以及6-叠氮-6-脱氧-D-半乳糖酸-1,4-内酯22的高效制备都说明了这种易得中间体的价值。将22转化为七元半乳糖内酰胺21（一种四羟基己内酰胺）可得到羟基化尼龙聚合物。半乳糖内酰胺21对多种糖苷酶没有明显的抑制作用。22与三氟甲磺酸酐反应可生成两种外消旋5-（叠氮甲基）四氢呋喃-2-羧酸酯，它们可作为两种系列碳青霉烯类药物的起始原料
• 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.