(3R,4S,5R,6s)-2,2-bis-(hydroxymethyl)azepane-3,4,5,6-tetraol hydrochloride | 1107060-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4S,5R,6s)-2,2-bis-(hydroxymethyl)azepane-3,4,5,6-tetraol hydrochloride
• 英文别名: (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol hydrochloride；(3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetrol;hydrochloride
• CAS: 1107060-45-6
• 化学式: C₈H₁₇NO₆*ClH
• 分子量: 259.687
• InChiKey: HHQQHNOCVCTXTJ-JIAUUHBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.82
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  133
• 氢给体数：
  8
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 甲醇 、 乙酰氯 作用下， 反应 0.5h， 以0.028 g的产率得到(3R,4S,5R,6s)-2,2-bis-(hydroxymethyl)azepane-3,4,5,6-tetraol hydrochloride
  参考文献：
  名称：

  Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol

  摘要：

  The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyi)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2 -O-isopropyIidene-6-nitro-alpha-D-glucofuranose with formaldehyde followed by a reductive ring closure to give the first branched 1,6-dideoxy-1,6-heptitol described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.027

文献信息

• Indium-Mediated Reaction of 1-Bromo-1-nitroalkanes with Aldehydes: Access to 2-Nitroalkan-1-ols
  作者：Raquel G. Soengas、Amalia M. Estévez

  DOI：10.1002/ejoc.201000662

  日期：2010.9

  A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel

  报道了一种通过溴硝基甲烷与多种醛的铟促进反应制备 2-nitroalkan-1-ols 的新方法。该反应也用 2-溴-2-硝基丙烷进行，得到 2,2-二烷基-2-硝基烷-1-醇。手性糖衍生醛的使用为相应的 2-nitroalkan-1-ols 提供了出色的立体选择性。新的糖衍生的 2,2-二烷基-2-硝基烷-1-醇用于制备支化亚氨基糖衍生物的效用通过羟甲基支化多羟基化氮杂环庚烷的制备得到证明。