(2R,3R)-1,2-O-cyclohexylidene-3-nitromethyl-propane-1,2,3-triol | 1248572-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-1,2-O-cyclohexylidene-3-nitromethyl-propane-1,2,3-triol
• 英文别名: (1R)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-2-nitroethanol
• CAS: 1248572-40-8
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: FHCXFDYEIWFHKV-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以89.3%的产率得到(2R,3S)-1,2-O-cyclohexylidene-3-nitromethyl-propane-1,2,3-triol
  参考文献：
  名称：

  Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: a simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B)

  摘要：

  (R)-2,3-Cyclohexylideneglyceraldehyde 1 has been found to be a good substrate for nitroaldol reaction both in anhydrous and aqueous conditions. In both cases, the reaction took place with good substrate-controlled anti-selectivity. The major nitroaldol product 2b has been exploited to develop a simple and stereoselective synthesis of jaspine B X. Also, beginning with nitroaldol reaction of 1, this route presents a simple approach for the stereoselective preparation of (anti-anti-5,7)- and (syn-syn-9, 11, 12)-1,2,3,4-alkanetetrols, each possessing three contiguous oxygenated stereocenters. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.024

文献信息

• Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: a simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B)
  作者：Prasad Vichare、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2010.06.024

  日期：2010.8

  (R)-2,3-Cyclohexylideneglyceraldehyde 1 has been found to be a good substrate for nitroaldol reaction both in anhydrous and aqueous conditions. In both cases, the reaction took place with good substrate-controlled anti-selectivity. The major nitroaldol product 2b has been exploited to develop a simple and stereoselective synthesis of jaspine B X. Also, beginning with nitroaldol reaction of 1, this route presents a simple approach for the stereoselective preparation of (anti-anti-5,7)- and (syn-syn-9, 11, 12)-1,2,3,4-alkanetetrols, each possessing three contiguous oxygenated stereocenters. (C) 2010 Elsevier Ltd. All rights reserved.