(Z)-3-deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-D-xylohexofuranose | 1610619-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-D-xylohexofuranose
• CAS: 1610619-27-6
• 化学式: C₁₃H₁₉NO₇
• 分子量: 301.296
• InChiKey: JGPCZCHLFMCGOF-UWNHXEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-D-xylohexofuranose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以80%的产率得到(3R)-3-deoxy-3-C-nitromethyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose
  参考文献：
  名称：

  Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses

  摘要：

  A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2: 5,6-di-O-isopropylidene-alpha-D-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration-rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.003
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 吡啶 、 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 乙酸酐 、 碳酸氢钠 、 sodium bromide 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 (Z)-3-deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-D-xylohexofuranose 、 (E)-3-deoxy-3-C-nitromethylene-1,2:5,6-di-O-isopropylidene-α-D-xylohexofuranose
  参考文献：
  名称：

  Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses

  摘要：

  A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2: 5,6-di-O-isopropylidene-alpha-D-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration-rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.003