(3R)-3-deoxy-3-C-nitromethyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose | 1610619-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3-deoxy-3-C-nitromethyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(nitromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1610619-26-5
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: KOSHLFBATSMVME-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-threo-D-glycero-3-hexofuranosulose 在 sodium tetrahydroborate 、 乙酸酐 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 (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

文献信息

• Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses
  作者：Māris Turks、Krista Vēze、Gļebs Kiseļovs、Jevgeņija Mackeviča、Jevgeņija Lugiņina、Anatoly Mishnev、Dean Marković

  DOI：10.1016/j.carres.2014.03.003

  日期：2014.6

  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.