(1S)-D-mannitol,1,5-anhydro-1-C-1H-perimidin-2-yl-2,3,4,6-tetraacetate | 1173900-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (1S)-D-mannitol,1,5-anhydro-1-C-1H-perimidin-2-yl-2,3,4,6-tetraacetate
• 英文别名: 2-(2',3',4',6'-tetra-O-acetyl-D-mannopyranosyl)perimidine；2-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)perimidime；[(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-(1H-perimidin-2-yl)oxan-2-yl]methyl acetate
• CAS: 1173900-59-8
• 化学式: C₂₅H₂₆N₂O₉
• 分子量: 498.489
• InChiKey: LHPGPJGXSPUSFN-SAKKWRDPSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,8-二氨基萘 、 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-1-chloro-1-hydroxymino-D-glycero-D-galacto-heptitol 以 乙醇 为溶剂， 反应 15.0h， 以55%的产率得到(1S)-D-mannitol,1,5-anhydro-1-C-1H-perimidin-2-yl-2,3,4,6-tetraacetate
  参考文献：
  名称：

  基于一氧化氮化学方法制备2-取代的嘧啶的新途径

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2009.04.118

文献信息

• 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.