(2R,4R,5R)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)-isopropylidene ketal-pyrrolidine | 490015-41-3

• 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-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)-isopropylidene ketal-pyrrolidine
• 英文别名: benzyl (4aR,6R,7aR)-6-(2-methoxy-2-oxoethyl)-2,2-dimethyl-4a,6,7,7a-tetrahydro-4H-[1,3]dioxino[5,4-b]pyrrole-5-carboxylate
• CAS: 490015-41-3
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: IMSXKPCIEUJFGH-BZUAXINKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 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-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)-isopropylidene ketal-pyrrolidine 在 咪唑 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 42.5h， 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：

  ((4aR,6R,7aR)-5-Benzenesulfonyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-6-yl)-acetic acid methyl ester 在 sodium naphthalenide 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (2R,4R,5R)-4-hydroxy-5-hydroxymethyl-2-methoxycarbonylmethyl-1-(benzyloxycarbonyl)-isopropylidene ketal-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.