(1R,2S,3S,4R,5S,6S)-5-(hydroxymethyl)-6-(methylamino)cyclohexane-1,2,3,4-tetraol hydrochloride | 138560-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,4R,5S,6S)-5-(hydroxymethyl)-6-(methylamino)cyclohexane-1,2,3,4-tetraol hydrochloride
• 英文别名: 1,2-dideoxy-2-(hydroxymethyl)-1-(methylamino)-myo-inositol hydrochloride
• CAS: 138560-22-2
• 化学式: C₈H₁₇NO₅*ClH
• 分子量: 243.688
• InChiKey: QPLUZHMSJCBPSZ-SQBYXQFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.94
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  113.18
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose 在 钯 N-氯代丁二酰亚胺 、 氢气 、 silver nitrate 作用下， 以 甲醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 52.75h， 生成 (1R,2S,3S,4R,5S,6S)-5-(hydroxymethyl)-6-(methylamino)cyclohexane-1,2,3,4-tetraol hydrochloride
  参考文献：
  名称：

  Diastereoselectivity in the intramolecular nitrone, oxime, and nitrile oxide cycloaddition reactions. Synthesis of amino inositol derivatives as α-glucosidase inhibitors

  摘要：

  The diastereoselectivity in the intramolecular 1,3-dipolar cycloaddition reactions of 4 and 5 (R = Bn, 4-MeOBn) was examined.

  DOI：

  10.1016/s0040-4020(01)88278-8

文献信息

• An unexpected access to 5-epi-cyclophellitol: a new cyclitol member
  作者：Pedro Serrano、Meritxell Egido-Gabás、Amadeu Llebaria、Antonio Delgado

  DOI：10.1016/j.tetasy.2007.08.002

  日期：2007.8

  A thorough reinvestigation of the hydroboration-oxidation of methylene epoxycyclohexane 3 has revealed the formation of a direct precursor of the hitherto unreported 5-epi-cyclophellitol. Hydroboration of the starting precursor 3 takes place with total and opposite stereocontrol to that previously described in the literature. The sterochemistry of this new cyclophellitol isomer has been unambiguously confirmed by comparison with reference compounds obtained by independent methods. (c) 2007 Elsevier Ltd. All rights reserved.