tert-butyl[{(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl}methoxy]diphenylsilane | 863976-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: tert-butyl[{(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl}methoxy]diphenylsilane
• 英文别名: [(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 863976-78-7
• 化学式: C₂₆H₃₆O₅Si
• 分子量: 456.654
• InChiKey: HJENGGAFGMVBMP-GDKQOWJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl[{(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl}methoxy]diphenylsilane 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 二苯基膦叠氮化物 、 氢气 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran
  参考文献：
  名称：

  Stereoselective Route to the Ezoaminuroic Acid Core of the Ezomycins

  摘要：

  Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.

  DOI：

  10.1021/jo051086n
• 作为产物：
  描述：

  (3R,4R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-3,4-dihydroxytetrahydropyran-2-one 在 三氟化硼乙醚 、 二异丁基氢化铝 、 silver(l) oxide 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 7.5h， 生成 tert-butyl[{(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl}methoxy]diphenylsilane
  参考文献：
  名称：

  Stereoselective Route to the Ezoaminuroic Acid Core of the Ezomycins

  摘要：

  Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.

  DOI：

  10.1021/jo051086n

文献信息

• Stereoselective Route to the Ezoaminuroic Acid Core of the Ezomycins
  作者：Juhienah K. Khalaf、Apurba Datta

  DOI：10.1021/jo051086n

  日期：2005.8.1

  Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.