(3aR,3bS,6R,7S,7aR,8aR)-7-Benzyloxyamino-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol | 325484-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (3aR,3bS,6R,7S,7aR,8aR)-7-Benzyloxyamino-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol
• 英文别名: (1S,2R,6R,8R,9S,10R)-4,4-dimethyl-9-(phenylmethoxyamino)-3,5,7,12-tetraoxatricyclo[6.4.0.02,6]dodecan-10-ol
• CAS: 325484-45-5
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: FXGAGTAYBWOVLY-RWHKXBQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  78.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,3bS,6R,7S,7aR,8aR)-7-Benzyloxyamino-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol 在 hexacarbonyl molybdenum 、 碳酸氢钠 作用下， 生成 ((3aR,3bS,6R,7S,7aR,8aR)-6-Hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-7-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Radical Cyclization of Oxime Ethers Derived from Monosaccharides Aiming at the Synthesis of Dysiherbaine and Related Stereoisomers

  摘要：

  Stannyl radical-mediated cyclization of oxime ethers (6), (14), (22), and (29) derived from glucose and galactose afforded the cyclized aminosugar derivatives (7), (8), (15, 16 and 17), (23), (24), and (30, 31 and 32) which would serve as key intermediates for the synthesis of dysiherbaine and its isomers.

  DOI：

  10.3987/com-00-9056
• 作为产物：
  描述：

  (3R,4S)-3-[(4R)-2,2-二甲基-1,3-二氧戊环-4-基]-7,7-二甲基-4-丙-2-烯氧基-2,6,8-三氧杂双环[3.3.0]辛烷 在 sodium periodate 、 四氧化锇 、 tribenzyltin hydride 、 偶氮二异丁腈 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 (3aR,3bS,6R,7S,7aR,8aR)-7-Benzyloxyamino-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol
  参考文献：
  名称：

  Radical Cyclization of Oxime Ethers Derived from Monosaccharides Aiming at the Synthesis of Dysiherbaine and Related Stereoisomers

  摘要：

  Stannyl radical-mediated cyclization of oxime ethers (6), (14), (22), and (29) derived from glucose and galactose afforded the cyclized aminosugar derivatives (7), (8), (15, 16 and 17), (23), (24), and (30, 31 and 32) which would serve as key intermediates for the synthesis of dysiherbaine and its isomers.

  DOI：

  10.3987/com-00-9056