(2R,3S,4R,5S)-3,4-dihydroxy-2-hydroxymethyl-1-oxa-7-azaspiro<4.4>nonane-6,8-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5S)-3,4-dihydroxy-2-hydroxymethyl-1-oxa-7-azaspiro<4.4>nonane-6,8-dione
• 英文别名: (2R,3S,4R,5S)-3,4-dihydroxy-2-(hydroxymethyl)-1-oxa-7-azaspiro[4.4]nonane-6,8-dione
• 化学式: C₈H₁₁NO₆
• 分子量: 217.178
• InChiKey: XFOYRZDSXRMGHT-OVBCRYSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3S,4R,5S)-2-benzyloxymethyl-3,4-dihydroxy-1-oxa-7-azaspiro<4.4>nonane-6,8-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 55.0 ℃ 、294.17 kPa 条件下， 反应 6.0h， 以60%的产率得到(2R,3S,4R,5S)-3,4-dihydroxy-2-hydroxymethyl-1-oxa-7-azaspiro<4.4>nonane-6,8-dione
  参考文献：
  名称：

  Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin

  摘要：

  Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethlsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.

  DOI：

  10.1016/0040-4020(94)01027-w

文献信息

• Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin
  作者：Hiromi Sano、Shigeru Mio、Naoto Tsukaguchi、Soji Sugai

  DOI：10.1016/0040-4020(94)01027-w

  日期：1995.1

  Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl4-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethlsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.