(2R,4R,5R)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)pyrrolidine | 490015-42-4

• 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,4R,5R)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)pyrrolidine
• 英文别名: benzyl (2R,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate
• CAS: 490015-42-4
• 化学式: C₂₈H₄₉NO₆Si₂
• 分子量: 551.871
• InChiKey: ALFLHSWJZBODSH-WXFUMESZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R,4R,5R)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)pyrrolidine 在 ruthenium trichloride 、 sodium periodate 、 溶剂黄146 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 29.0h， 生成 (2R,4R,5R)-4-tert-butyldimethylsilyloxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Asymmetric Synthesis of the Carbapenam Core from Serine

  摘要：

  The stereospecific synthesis of the functionalized carbapenam core 16 from the serine-derived trisubstituted pyrrolidine 9 is reported. The synthetic strategy relies on synthesizing an appropriately functionalized pyrrolidine, followed by an intramolecular azetidone formation utilizing a modified Mukiyama reagent. The efficient one-pot conversion of the benzenesulfonamide-protected pyrrolidine 9 to the Cbz-protected pyrrolidine 10 is also reported.

  DOI：

  10.1021/jo026499s
• 作为产物：
  描述：

  (2R,4R,5R)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)-isopropylidene ketal-pyrrolidine 在 咪唑 、 盐酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (2R,4R,5R)-4-tert-butyldimethylsilyloxy-5-tert-butyldimethylsilyloxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Asymmetric Synthesis of the Carbapenam Core from Serine

  摘要：

  The stereospecific synthesis of the functionalized carbapenam core 16 from the serine-derived trisubstituted pyrrolidine 9 is reported. The synthetic strategy relies on synthesizing an appropriately functionalized pyrrolidine, followed by an intramolecular azetidone formation utilizing a modified Mukiyama reagent. The efficient one-pot conversion of the benzenesulfonamide-protected pyrrolidine 9 to the Cbz-protected pyrrolidine 10 is also reported.

  DOI：

  10.1021/jo026499s

文献信息

• Asymmetric Synthesis of the Carbapenam Core from Serine
  作者：Barry P. Hart、Sharad K. Verma、Henry Rapoport

  DOI：10.1021/jo026499s

  日期：2003.1.1

  The stereospecific synthesis of the functionalized carbapenam core 16 from the serine-derived trisubstituted pyrrolidine 9 is reported. The synthetic strategy relies on synthesizing an appropriately functionalized pyrrolidine, followed by an intramolecular azetidone formation utilizing a modified Mukiyama reagent. The efficient one-pot conversion of the benzenesulfonamide-protected pyrrolidine 9 to the Cbz-protected pyrrolidine 10 is also reported.