3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxymino-D-glycero-D-gulo-heptitol | 357265-77-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxymino-D-glycero-D-gulo-heptitol
• 英文别名: glucopyranosyl-hydroximoyl chloride
• CAS: 357265-77-1
• 化学式: C₁₅H₂₀ClNO₁₀
• 分子量: 409.778
• InChiKey: FXPKPGVAHAARHI-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxymino-D-glycero-D-gulo-heptitol 在 三乙胺 作用下， 以 乙醚 为溶剂， 以96%的产率得到3,4-di(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  3,4-二吡喃糖基-1,2,5-恶二唑2-氧化物：合成与X射线结构

  摘要：

  3，4-二（2,3,4,6-四-O-乙酰基-β-d-甘露吡喃糖基）-1,2,5-恶二唑2-氧化物（7）是通过以下方法由d-甘露糖合成的作为关键步骤涉及甘露吡喃糖基一氧化氮2的二聚。三种方法用于生成一氧化氮：异氰酸酯介导的硝基甲基甘露糖衍生物4脱水，用盐酸水溶液处理醛肟5。次氯酸盐，和碱诱导的羟肟酰氯6的脱氯化氢作用。d-葡糖，d半乳糖，d-木糖和L- fucopyranosyl类似物8 - 11类似地制备。d-甘露糖衍生的1,2,5-恶二唑2-氧化物7的结构 通过X射线晶体学确定。

  DOI：

  10.1016/s0040-4020(02)01023-2
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(nitro)methane 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 、 氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxymino-D-glycero-D-gulo-heptitol
  参考文献：
  名称：

  新型酰胺肟连接的假二糖的合成

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2010.10.174

文献信息

• Generation and cycloaddition reactions of pyranose-1-carbonitrile oxides
  作者：Kenneth W.J Baker、Andrew Gibb、Andrew R March、R.Michael Paton

  DOI：10.1016/s0040-4039(01)00631-1

  日期：2001.6

  Stannate(II) reduction of the β-d-glucopyranosylnitromethane derivative 4 affords aldoxime 5, which provides access to the nitrile oxide 7, either on treatment with aq. hypochlorite, or via conversion to the hydroximoyl chloride 11 followed by base-mediated dehydrohalogenation. d-Galactose-, d-mannose- and d-xylose-derived nitrile oxides are generated similarly. The nitrile oxides either dimerise to

  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。
• Synthesis of pyranosyl amidoximes by addition of amines to pyranosyl nitrile oxides
  作者：Kenneth W.J. Baker、Katherine S. Horner、Stephen A. Moggach、R. Michael Paton、Iain A.S. Smellie

  DOI：10.1016/j.tetlet.2004.09.173

  日期：2004.11

  Addition of amines to pyranosyl nitrile oxides, generated by base-induced dehydrochlorination of the corresponding hydroximoyl chloride, affords pyranosyl N-alkyl/aryl-formamide oximes (41–90%). Reaction with amino acid esters yields the corresponding amidoximes and/or 3-pyranosyl-1,2,4-oxadiazin-6-ones. The structure of N-phenyl-C-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)formamide oxime was established

  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。
• 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 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.