3,4,5-tri-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxyimino-D-gluco-hexitol | 811434-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3,4,5-tri-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxyimino-D-gluco-hexitol
• CAS: 811434-27-2
• 化学式: C₁₂H₁₆ClNO₈
• 分子量: 337.714
• InChiKey: WOFTYQJVTDOUNX-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120.72
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4,5-tri-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxyimino-D-gluco-hexitol 在 三乙胺 作用下， 生成
  参考文献：
  名称：

  通过将胺加到吡喃糖基腈氧化物中来合成吡喃糖基mid胺肟

  摘要：

  由碱诱导的相应羟肟基氯的脱氯化氢反应生成的吡喃糖基腈氧化物中加成胺，可得到吡喃糖基N-烷基/芳基甲酰胺肟（41-90％）。与氨基酸酯反应产生相应的酰胺肟和/或3-吡喃糖基-1，2，4-恶二嗪-6-酮。的结构Ñ苯基Ç - （2,3,4-三- ö乙酰基β-d-D-吡喃木糖基）甲酰胺肟，通过X射线晶体学确定。

  DOI：

  10.1016/j.tetlet.2004.09.173
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane 在 氯 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3,4,5-tri-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxyimino-D-gluco-hexitol
  参考文献：
  名称：

  吡喃糖-1-腈氧化物的产生和环加成反应

  摘要：

  β-d-吡喃葡萄糖基硝基甲烷衍生物4的Stannate（II）还原得到醛肟5，该醛肟在用NH 4 Cl水溶液处理时提供了与一氧化氮7的通道。次氯酸盐，或通过转化为羟肟基氯11，然后进行碱介导的脱卤化氢反应。d-半乳糖，d-甘露糖和d-木糖衍生的腈氧化物的生成方式相似。腈氧化物要么二聚为3,4-dipyranosyl-1,2,5- oxadiazole N-氧化物，要么在双极性亲和剂的存在下以环加成物形式被捕集。

  DOI：

  10.1016/s0040-4039(01)00631-1

文献信息

• A new route to 2-substituted perimidines based on nitrile oxide chemistry
  作者：Iain A.S. Smellie、Andreas Fromm、R. Michael Paton

  DOI：10.1016/j.tetlet.2009.04.118

  日期：2009.7

  A new route to perimidines has been developed which involves reaction of a nitrile oxide with 1,8-diaminonaphthalene. Benzonitrile oxide, generated by dehydrochlorination of benzohydroximoyl chloride, and 1,8-diaminonaphthalene afforded 2-phenylperimidine. 2-Pyranosylperimidines were prepared by the same approach from pyranosyl hydroximoyl chlorides.

  已开发出一种新的过碘im的方法，该方法涉及一氧化氮与1，8-二氨基萘的反应。通过苯甲酰氢氧肟基氯的脱氯化氢反应生成的氧化苯甲腈和1,8-二氨基萘得到2-苯基哌啶。用相同的方法由吡喃糖基羟基肟基氯制备2-吡喃糖基嘧啶。
• Synthesis of novel amidoxime-linked pseudodisaccharides
  作者：Iain A.S. Smellie、Stephen A. Moggach、R. Michael Paton

  DOI：10.1016/j.tetlet.2010.10.174

  日期：2011.1

  Disaccharide analogues containing amidoxime interglycosidic linkages have been synthesised by nucleophilic addition of aminomethylene pyranoses to pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides. The structure of the C-xylopyranosyl-N-galactopyranosyl amidoxime 1 was established by X-ray crystallography.

  含有a胺肟糖苷间键的二糖类似物是通过将氨基亚甲基吡喃糖类亲核加成到吡喃糖基腈类氧化物中而合成的，而吡喃糖基腈类氧化物是通过相应的羟肟基氯化物的脱氯化氢作用而生成的。所述的结构Ç -xylopyranosyl- Ñ -galactopyranosyl偕胺肟1通过X射线晶体学确定。
• Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides
  作者：Iain A.S. Smellie、Andreas Fromm、Francesca Fabbiani、Iain D.H. Oswald、Fraser J. White、R. Michael Paton

  DOI：10.1016/j.tet.2010.06.076

  日期：2010.8

  Reaction of per-O-acetylated-β-d-pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides, with 2-aminothiophenol afforded 2-(β-d-pyranosyl)benzothiazoles. 1,2-Diaminobenzene and 2-aminophenol reacted similarly to yield 2-(β-d-pyranosyl)benzimidazoles and 2-(β-d-pyranosyl)benzoxazoles, respectively. The structures of 2-β-d-glucopyranosylbenzimidazole (17)

  通过相应的羟基氧酰氯的脱氯化氢反应生成的过-O-乙酰化的β- d-吡喃基腈腈氧化物与2-氨基硫酚反应，得到2-（β- d-吡喃基）苯并噻唑。1,2-二氨基苯和2-氨基苯酚的反应相似，分别得到2-（β- d-吡喃基）苯并咪唑和2-（β- d-吡喃基）苯并恶唑。的2-β-结构d -glucopyranosylbenzimidazole（17），2-（2,3,4-三- ø -乙酰基β- d -xylopyranosyl）苯并咪唑（19）和所述thiohydroximate吡喃木糖13 是由X射线建立晶体学。
• Synthesis and structure of 2-pyransoylperimidines
  作者：Iain A.S. Smellie、Andreas Fromm、Stephen A. Moggach、R. Michael Paton

  DOI：10.1016/j.carres.2010.09.028

  日期：2011.1

  The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.