2,3,4-tri-O-acetyl-β-D-xylopyranosylmethanal oxime | 586367-81-9

• 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: 2,3,4-tri-O-acetyl-β-D-xylopyranosylmethanal oxime
• 英文别名: 2,3,4-tri-O-acetyl-β-D-xylopyranosylformaldoxime；tri-O-acetyl-β-D-xylopyranosylformaldoxime；3,4,5-tri-O-acetyl-2,6-anhydro-D-gulose oxime
• CAS: 586367-81-9
• 化学式: C₁₂H₁₇NO₈
• 分子量: 303.269
• InChiKey: HYSSQZITNVSSJJ-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  21.0
• 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：

  2,3,4-tri-O-acetyl-β-D-xylopyranosylmethanal oxime 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 以89%的产率得到3,4-di(2,3,4,6-tetra-O-acetyl-β-D-xylopyranosyl)-1,2,5-oxadiazole 2-oxide
  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
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-β-D-xylopyranosyl(nitro)methane 在 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2,3,4-tri-O-acetyl-β-D-xylopyranosylmethanal oxime
  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

• 3,4-Dipyranosyl-1,2,5-oxadiazole 2-oxides: synthesis and X-ray structure
  作者：Kenneth W.J Baker、Andrew R March、Simon Parsons、R.Michael Paton、Gavin W Stewart

  DOI：10.1016/s0040-4020(02)01023-2

  日期：2002.10

  has been synthesised from d-mannose by a route involving as the key step dimerisation of mannopyranosyl nitrile oxide 2. Three methods were used for the generation of the nitrile oxide: isocyanate-mediated dehydration of nitromethylmannose derivative 4, treatment of aldoxime 5 with aq. hypochlorite, and base-induced dehydrochlorination of hydroximoyl chloride 6. d-Gluco, d-galacto, d-xylo, and l-fucopyranosyl

  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。
• One-Step Conversion of <i>C</i>-Glycopyranosylnitromethanes to the Corresponding Methanal Oximes
  作者：Duy-Phong Pham-Huu、Mária Petrušová、James N. BeMiller、Ladislav Petruš

  DOI：10.1055/s-1998-1950

  日期：1998.12

  A novel method for preparation of C-glycopyranosylmethanal oximes is described. Treatment of per-O-acetylated C-glycopyranosylnitromethanes of the β-D-gluco, β-D-manno, β-D-galacto, β-D-xylo, and β-L-rhamno configurations with tributyltin hydride and a catalytic amount of 1,1′-azobis(cyclohexanecarbonitrile) afforded the corresponding methanal oximes in isolated yields of 84-97%.

  本文介绍了一种制备 C-吡喃糖基甲醛肟的新方法。用氢化三丁基锡和催化量的 1,1′-偶氮双（环己烷甲腈）处理δ-D-葡糖基、δ-D-甘露糖基、δ-D-半乳糖基、δ-D-氧代和δ-L-鼠李糖基构型的过 O-乙酰化 C-吡喃糖基硝基甲烷，可得到相应的甲醛肟，分离产率为 84-97%。
• 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.
• A Convenient Synthesis <b>o</b>f Pyranosyl-1-carbaldoximes
  作者：Kenneth W. J. Baker、Andrew Gibb、Andrew R. March、Simon Parsons、R. Michael Paton

  DOI：10.1081/scc-120018932

  日期：2003.1.6

  A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.