(3aS,5S,6R,6aS)-5-Benzyl-6-formyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyrrole-4-carboxylic acid benzyl ester | 201678-23-1

• 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: (3aS,5S,6R,6aS)-5-Benzyl-6-formyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyrrole-4-carboxylic acid benzyl ester
• 英文别名: benzyl (3aS,5S,6R,6aS)-5-benzyl-6-formyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydro-[1,3]dioxolo[4,5-b]pyrrole-4-carboxylate
• CAS: 201678-23-1
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: FBVWJGLCERALBP-WOZUAGRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,5S,6R,6aS)-5-Benzyl-6-formyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyrrole-4-carboxylic acid benzyl ester 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (2S,3R,4R,5S)-2-Allyl-5-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-4-formyloxy-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Diastereoselective Formal Synthesis of the Antifungal Agent, (+)-Preussin. A New Entry to Chiral Pyrrolidines

  摘要：

  A formal total synthesis of (+)-Preussin was achieved by using D-mannose as the starting material. The key step involved diastereoselective addition of allyltrimethylsilane to the bicyclic ketal 5. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10468-3
• 作为产物：
  描述：

  (3aS,4S,6R,6aS)-4-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-6-(oxiran-2-yl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium azide 、 亚碘酰苯 、 水 、 碘 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (3aS,5S,6R,6aS)-5-Benzyl-6-formyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyrrole-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  Diastereoselective Formal Synthesis of the Antifungal Agent, (+)-Preussin. A New Entry to Chiral Pyrrolidines

  摘要：

  A formal total synthesis of (+)-Preussin was achieved by using D-mannose as the starting material. The key step involved diastereoselective addition of allyltrimethylsilane to the bicyclic ketal 5. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10468-3

文献信息

• Highly 2,3-<i>trans</i> Stereoselective Allylations of 2,3-<i>O</i>-Isopropylidene-Protected Pyrrolidines:  Circumventing the <i>N</i>-Acyliminium Ion Chemistry?
  作者：Pedro de Armas、Fernando García-Tellado、José Juan Marrero-Tellado

  DOI：10.1021/ol006574q

  日期：2000.11.1

  [GRAPHICS]A remarkable exo-facial template effect exercised by a 2,3-O-isopropylidene protective group is the key for the entire 2,3-trans stereoselectivity observed in the allylsilane addition promoted by BF3. OEt2 to 2,3-O-isopropylidene-protected pyrrolidines.
• Diastereoselective Formal Synthesis of the Antifungal Agent, (+)-Preussin. A New Entry to Chiral Pyrrolidines
  作者：Pedro de Armas、Fernando García-Tellado、José J. Marrero-Tellado、Juana Robles

  DOI：10.1016/s0040-4039(97)10468-3

  日期：1998.1

  A formal total synthesis of (+)-Preussin was achieved by using D-mannose as the starting material. The key step involved diastereoselective addition of allyltrimethylsilane to the bicyclic ketal 5. (C) 1997 Elsevier Science Ltd. All rights reserved.