(3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[(R)-1-hydroxy-3-(N-methylamino)-3-oxopropyl]pyrrolidine | 171094-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[(R)-1-hydroxy-3-(N-methylamino)-3-oxopropyl]pyrrolidine
• 英文别名: tert-butyl (2S,4R)-4-hydroxy-2-[(1R)-1-hydroxy-3-(methylamino)-3-oxopropyl]pyrrolidine-1-carboxylate
• CAS: 171094-64-7
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: HQDCBOAKIWNWAM-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[(R)-1-hydroxy-3-(N-methylamino)-3-oxopropyl]pyrrolidine 在 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成 (3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[(R)-1-hydroxy-3-(N-tert-butoxycarbonyl-N-methylamino)propyl]pyrrolidine
  参考文献：
  名称：

  Diastereoselective synthesis of the key intermediate of the BO-2727 side chain

  摘要：

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00315-7
• 作为产物：
  描述：

  (3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[3-(N-methylamino)-1,3-dioxopropyl]pyrrolidine 在 盐酸 、 RuCl₂[(S)-BINAP] 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 25.0~62.0 ℃ 、490.29 kPa 条件下， 反应 48.0h， 生成 (3R,5S)-N-tert-butoxycarbonyl-3-hydroxy-5-[(R)-1-hydroxy-3-(N-methylamino)-3-oxopropyl]pyrrolidine
  参考文献：
  名称：

  Diastereoselective synthesis of the key intermediate of the BO-2727 side chain

  摘要：

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00315-7

文献信息

• An efficient asymmetric synthesis of the mercaptopyrrolidine side chain of an important β-methyl carbapenem antibiotic
  作者：Joseph D. Armstrong、Jennifer L. Keller、Joseph Lynch、Tom Liu、Frederick W. Hartner、Norikazu Ohtake、Shigemitsu Okada、Yasuyuki Imai、Osamu Okamoto、Ryosuke Ushijima、Susumu Nakagawa、R.P. Volante

  DOI：10.1016/s0040-4039(97)00613-8

  日期：1997.5

  An efficient asymmetric synthesis of the mercaptopyrrolidine side chain 2 1s described. The β-ketoester 4 is hydrogenated diastereoselectively to give the (R)-β-hydroxyester 5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produce 2 in 34% overall yield from BOC-L-trans-4-hydroxyproline methylester 3 (Scheme 1).

  描述了巯基吡咯烷侧链2 1s的有效不对称合成。β-酮酯4非对映选择性地氢化，得到（R）-β-羟基酯5。剩余的官能团通过硫醇Mitsunobu反应和仲酰胺的还原而安装，从而从BOC-L-trans-4-羟基脯氨酸甲酯3（方案1）中以34％的总收率产生2个。
• Diastereoselective synthesis of the key intermediate of the BO-2727 side chain
  作者：Norikazu Ohtake、Hideki Jona、Shigemitsu Okada、Osamu Okamoto、Yasuyuki Imai、Ryosuke Ushijima、Susumu Nakagawa

  DOI：10.1016/s0957-4166(97)00315-7

  日期：1997.9

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.