(2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one | 156045-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one
• 英文别名: (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo[3.3.0]octane-8-one；(3R,7S,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 156045-80-6
• 化学式: C₁₈H₂₇NO₃Si
• 分子量: 333.503
• InChiKey: FEFITDFKOWYKLP-HLLBOEOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one 在 palladium on activated charcoal 四甲基乙二胺 、 dimethyl sulfide borane 、 氢气 作用下， 以 甲醇 为溶剂， 25.0~70.0 ℃ 、2.0 MPa 条件下， 反应 11.0h， 生成 tert-butyl (2R,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9
• 作为产物：
  描述：

  (3R,7aS)-3-phenyl-6-(phenylselanyl)tetrahydro-3H,5H-pyrrolo[1,2-c]oxazol-5-one 在 咪唑 、 叔丁基过氧化氢 、 aluminium amalgam 、 四丁基氟化铵 、 双氧水 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 异辛烷 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.67h， 生成 (2R,5R,6S)-6-tert-butyldimethylsiloxy-3-oxa-2-phenyl-1-azabicyclo<3.3.0>octane-8-one
  参考文献：
  名称：

  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.

  摘要：

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.

  DOI：

  10.1016/s0957-4166(00)80492-9

文献信息

• Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid.
  作者：Claus Herdeis、Hans Peter Hubmann、Hermann Lotter

  DOI：10.1016/s0957-4166(00)80492-9

  日期：1994.1

  The Pyroglutamic acid derivative 1 was converted through several steps into Castanodiol 9 and 2S,3S-3-Hydroxyproline 11. Key steps of the reaction sequence were the stereoselective epoxidation of 1 to 2 and the regioselective ring opening of 2 to 3. BH3.S(CH3)(2) reduction of the amide group of 3 and 4 resulted in a concomitant transformation of the acetal moiety into the N-benzyl protecting group. The air sensitive 5 and 6, were transformed to the stable N-Boc prolinol derivatives 7 and 8. Deprotection of 8 provided 9, while oxidation of 8 gave the protected proline derivative 10. Deprotection of 10 furnished enantiopure 2S,3S-3-Hydroxyproline 11.