(4S,6R,8R,9S,10S,11R)-9,10,11-trihydroxy-8-(hydroxymethyl)-3-methyl-4-[(2S)-oxolan-2-yl]-1,7-dioxa-3-azaspiro[5.5]undecan-2-one | 1075227-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6R,8R,9S,10S,11R)-9,10,11-trihydroxy-8-(hydroxymethyl)-3-methyl-4-[(2S)-oxolan-2-yl]-1,7-dioxa-3-azaspiro[5.5]undecan-2-one
• CAS: 1075227-64-3
• 化学式: C₁₄H₂₃NO₈
• 分子量: 333.339
• InChiKey: MYURHRRMENOFNM-GQDTXSMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (4S,6R,8R,9R,10S,11R)-4-(furan-2-yl)-3-methyl-9,10,11-tris(phenylmethoxy)-8-(phenylmethoxymethyl)-1,7-dioxa-3-azaspiro[5.5]undecan-2-one 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以66.7%的产率得到(4S,6R,8R,9S,10S,11R)-9,10,11-trihydroxy-8-(hydroxymethyl)-3-methyl-4-[(2R)-oxolan-2-yl]-1,7-dioxa-3-azaspiro[5.5]undecan-2-one
  参考文献：
  名称：

  Stereoselective synthesis and biological activity of novel spiro-oxazinanone-C-glycosides

  摘要：

  The stereoselective synthesis of novel spiro-oxazinanone nucleosides 9 and 10 has been achieved by microwave assisted 1,3-dipolar cycloaddition of exo-glucal (1) and nitrones (2), and followed by reduction, stereospecific recyclization, and catalytic deprotection. The structures of the spironucleosides were determined according to the H-1 NMR, C-13 NMR, 2D NMR, MS, and X-ray analyses, and the biological activities of the title compounds against glycosidases (alpha-amylase, alpha-glucosidase, and beta-glucosidase) and cytotoxicity were also evaluated. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.002

文献信息

• Stereoselective synthesis and biological activity of novel spiro-oxazinanone-C-glycosides
  作者：Xiaoliu Li、Rui Wang、Yanpo Wang、Hua Chen、Zhiwei Li、Cuilan Ba、Jinchao Zhang

  DOI：10.1016/j.tet.2008.08.002

  日期：2008.10

  The stereoselective synthesis of novel spiro-oxazinanone nucleosides 9 and 10 has been achieved by microwave assisted 1,3-dipolar cycloaddition of exo-glucal (1) and nitrones (2), and followed by reduction, stereospecific recyclization, and catalytic deprotection. The structures of the spironucleosides were determined according to the H-1 NMR, C-13 NMR, 2D NMR, MS, and X-ray analyses, and the biological activities of the title compounds against glycosidases (alpha-amylase, alpha-glucosidase, and beta-glucosidase) and cytotoxicity were also evaluated. (C) 2008 Elsevier Ltd. All rights reserved.