(+)-(1S,2R,3R,4R)-2,3-diazido-1,4-dimethoxycyclohex-5-ene | 347837-89-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物
• 英文名称: (+)-(1S,2R,3R,4R)-2,3-diazido-1,4-dimethoxycyclohex-5-ene
• 英文别名: (3S,4R,5R,6R)-4,5-diazido-3,6-dimethoxycyclohexene
• CAS: 347837-89-2
• 化学式: C₈H₁₂N₆O₂
• 分子量: 224.222
• InChiKey: BHRNJGNADLOWHV-YWIQKCBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R,3R,4R)-2,3-diazido-1,4-dimethoxycyclohex-5-ene 在 1,3-丙二硫醇 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以70%的产率得到(+)-(1S,2R,3R,4R)-2,3-diamino-1,4-dimethoxycyclohex-5-ene
  参考文献：
  名称：

  Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols

  摘要：

  A new 2,3-diamino conduritol, isoster of conduritol F, was obtained starting from D-sorbitol. In the synthetic sequence an unprecedented transannular cyclization led, as a side product, to a bicyclic compound bearing a cyclopropyl ring. The synthesis of the completely deprotected 2,3-diamino conduritol, isoster of conduritol B, was devised via the intermediate O-benzylation of the OH groups. The O-methylated and deprotected 2,3-diamino conduritols were evaluated as inhibitors of alpha- and beta -glucosidase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00188-0
• 作为产物：
  描述：

  1,6-Anhydo-2,5-di-O-methyl-1(6)-thio-L-idit 在 吡啶 、 氢氧化钾 、 sodium azide 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 25.0h， 生成 (+)-(1S,2R,3R,4R)-2,3-diazido-1,4-dimethoxycyclohex-5-ene
  参考文献：
  名称：

  Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols

  摘要：

  A new 2,3-diamino conduritol, isoster of conduritol F, was obtained starting from D-sorbitol. In the synthetic sequence an unprecedented transannular cyclization led, as a side product, to a bicyclic compound bearing a cyclopropyl ring. The synthesis of the completely deprotected 2,3-diamino conduritol, isoster of conduritol B, was devised via the intermediate O-benzylation of the OH groups. The O-methylated and deprotected 2,3-diamino conduritols were evaluated as inhibitors of alpha- and beta -glucosidase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00188-0