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

• 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。
• Straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/s0957-4166(03)00588-3

  日期：2003.9

  High yielding routes for the synthesis of selectively protected derivatives Of D- and L-galactonic acids. having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono- 1.4-lactones was developed as a key step of the sequence. For example. 6-azido-6-deoxy-L-galactono- 1.4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, Mel) to the methyl ester of the 2,3.4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 Of L-galactonolactone 1 and isopropylidenation followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.