methyl (3R,4S,5S,7S,8R,9R)-8,9-isopropylidenedioxy-2-methyl-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenyl-1,6-dioxa-2-azaspiro[4.4]nonane-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: methyl (3R,4S,5S,7S,8R,9R)-8,9-isopropylidenedioxy-2-methyl-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenyl-1,6-dioxa-2-azaspiro[4.4]nonane-4-carboxylate
• 英文别名: methyl (3R,3'aR,4S,5S,6'S,6'aR)-6'-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2',2'-trimethyl-3-phenylspiro[1,2-oxazolidine-5,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-4-carboxylate
• 化学式: C₂₃H₃₁NO₈
• 分子量: 449.501
• InChiKey: NQSQZMOLIQIAGJ-VEOBLWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S,5S,7S,8R,9R)-8,9-isopropylidenedioxy-2-methyl-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenyl-1,6-dioxa-2-azaspiro[4.4]nonane-4-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以90%的产率得到(3'R,3aR,4S,4'S,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]dihydro-2,2,2'-trimethyl-3'-phenyl-spiro[furo[3,4-d]-1,3-dioxole-4(3aH)-5'-isoxazolidine]-4'-carboxylic acid
  参考文献：
  名称：

  Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design

  摘要：

  Spiro sugar-isoxazolidines obtained by 1,3-dipolar cycloaddition of activated exo-glycals and nitrones were efficiently functionalized at two sites, i.e. C-4 and C-7, with arginine, arginine mimetics and guanidylated appendages. Two bicyclic sugar derivatives differing by the configuration at C-7 were chosen as model compounds. The small library of peptidomimetics was evaluated toward inhibition of VEGF-A165/neuropilin-1 binding. Unexpected cleavage of C3-C4 bond of isoxazolidine moiety was observed during hydrogenolysis and opened thus a new way toward hemiketal structures which could also find interesting applications as less constrained scaffold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.01.005
• 作为产物：
  描述：

  N-methyl-α-phenylnitrone 、 methyl (2Z)-2-[(3aR,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-ylidene]acetate 以 甲苯 为溶剂， 反应 2.0h， 以33.333%的产率得到
  参考文献：
  名称：

  Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design

  摘要：

  Spiro sugar-isoxazolidines obtained by 1,3-dipolar cycloaddition of activated exo-glycals and nitrones were efficiently functionalized at two sites, i.e. C-4 and C-7, with arginine, arginine mimetics and guanidylated appendages. Two bicyclic sugar derivatives differing by the configuration at C-7 were chosen as model compounds. The small library of peptidomimetics was evaluated toward inhibition of VEGF-A165/neuropilin-1 binding. Unexpected cleavage of C3-C4 bond of isoxazolidine moiety was observed during hydrogenolysis and opened thus a new way toward hemiketal structures which could also find interesting applications as less constrained scaffold. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.01.005

文献信息

• Cycloaddition reactions on activated exo-glycals
  作者：Gérald Enderlin、Claude Taillefumier、Claude Didierjean、Yves Chapleur

  DOI：10.1016/j.tetasy.2005.06.027

  日期：2005.7

  Cycloaddition reactions of activated exo-glycals and nitrones proceeded only under microwave activation, with excellent facial selectivities on furanoglycosylidenes and good stereocontrol on the nitrone producing only two diastereomeric spiroisoxazolidines. alpha/beta-Spiro sugar-isoxazolidines are obtained from pyrano exo-glycals. The cycloaddition reaction with nitrile oxide proceeds at room temperature and gives open-chain isoxazoles due to facile beta-elimination of the sugar ring oxygen on the intermediate isoxazoline ring system. All the heterocycles obtained this way can be regarded as nucleoside analogues. (C) 2005 Elsevier Ltd. All rights reserved.
• Spiro sugar-isoxazolidine scaffold as useful polyfunctional building block for peptidomimetics design
  作者：Mylène Richard、Yves Chapleur、Nadia Pellegrini-Moïse

  DOI：10.1016/j.carres.2016.01.005

  日期：2016.3

  Spiro sugar-isoxazolidines obtained by 1,3-dipolar cycloaddition of activated exo-glycals and nitrones were efficiently functionalized at two sites, i.e. C-4 and C-7, with arginine, arginine mimetics and guanidylated appendages. Two bicyclic sugar derivatives differing by the configuration at C-7 were chosen as model compounds. The small library of peptidomimetics was evaluated toward inhibition of VEGF-A165/neuropilin-1 binding. Unexpected cleavage of C3-C4 bond of isoxazolidine moiety was observed during hydrogenolysis and opened thus a new way toward hemiketal structures which could also find interesting applications as less constrained scaffold. (C) 2016 Elsevier Ltd. All rights reserved.