t-butyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>pyroglutamate | 212970-89-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>pyroglutamate
• 英文别名: tert-butyl (2S,3S,4R)-N-tert-butoxycarbonyl-[3,4-2H2]pyroglutamate；tert-butyl (2S,3S,4R)-N-tert-butoxycarbonyl[3,4-D2]pyroglutamate；ditert-butyl (2S,3S,4R)-3,4-dideuterio-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 212970-89-3
• 化学式: C₁₄H₂₃NO₅
• 分子量: 287.324
• InChiKey: INVKHBRFFCQICU-MXKPUUNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  t-butyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>pyroglutamate 在 三乙基硼氢化锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 t-butyl (2S,3S,4R,5RS)-N-t-butoxycarbonyl-5-methoxy<3,4-D2>prolinate
  参考文献：
  名称：

  Stereodivergent Synthesis of (2S,3S,4R,5R)- and (2S,3S,4R,5S)-[3,4,5-D₃]Proline Depending on the Substituent of the γ-Lactam Ring

  摘要：

  DOI：

  10.1021/jo990866r
• 作为产物：
  描述：

  1,2-di-tert-butyl (2S)-2,5-dihydropyrrole-1,2-dicarboxylate 在 Ru-carbon ruthenium(IV) oxide 、 sodium periodate 、 氘 作用下， 以 氘代甲醇-d 、 乙酸乙酯 为溶剂， 25.0 ℃ 、506.62 kPa 条件下， 生成 t-butyl (2S,3S,4R)-N-t-butoxycarbonyl<3,4-D2>pyroglutamate
  参考文献：
  名称：

  Asymmetric synthesis of l-proline regio- and stereoselectively labelled with deuterium

  摘要：

  A synthesis of L-proline where all of the ring methylenes me stereoselectiveiy labelled with deuterium is described. A catalytic deuteration of protected 3,4-dehydro-L-proline using transition metal catalyst followed by RuO4-oxidation gave a [3,4-D-2]pyroglutamic acid derivative. A syn-selective deuteration of the aminal derived from the pyroglutamate with Et3SiD-BF3. OEt2 furnished (2S,3S,4R,5S)-[3,4,5-D-3]proline. The present procedure is also applied to the synthesis of the corresponding (2S,3S,4R,SR)-isomer. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00083-x

文献信息

• Convenient synthesis of deuterated glutamic acid, proline and leucine via catalytic deuteration of unsaturated pyroglutamate derivatives
  作者：Makoto Oba、Kosuke Ohkuma、Hiroshi Hitokawa、Ayumi Shirai、Kozaburo Nishiyama

  DOI：10.1002/jlcr.1038

  日期：2006.3.15

  Novel 3,4-didehydropyroglutamate derivatives, the key intermediates in this synthesis, were obtained from a protected pyroglutamate by the well-known selenenylation-oxidative deselenenylation method and were catalytically deuterated using a slow-addition technique. The obtained deuterated pyroglutamates were converted to [3,4-2H2]glutamic acid, [3,4,5-2H3]proline, and [3,4,5,5,5-2H5]leucine via an appropriate functional group interconversions followed by the standard deprotection procedure. Copyright © 2006 John Wiley & Sons, Ltd.

  通过著名的硒化-氧化脱硒化方法，从一种受保护的焦谷氨酸中获得了本合成中的关键中间体--新型 3,4-二idehydropyroglutamate（3,4-二idehydyroglutamate）衍生物，并利用慢加成技术对其进行了催化氚化。得到的氚化焦谷氨酸通过适当的官能团相互转化，然后通过标准的脱保护程序转换成[3,4-2H2]谷氨酸、[3,4,5-2H3]脯氨酸和[3,4,5,5,5-2H5]亮氨酸。Copyright © 2006 John Wiley & Sons, Ltd. 版权所有。
• Stereodivergent Synthesis of (<i>2S</i>,<i>3S</i>,<i>4R</i>,<i>5R</i>)- and (<i>2S</i>,<i>3S</i>,<i>4R</i>,<i>5S</i>)-[3,4,5-D₃]Proline Depending on the Substituent of the γ-Lactam Ring
  作者：Makoto Oba、Akiko Miyakawa、Kozaburo Nishiyama、Tsutomu Terauchi、Masatsune Kainosho

  DOI：10.1021/jo990866r

  日期：1999.12.1
• Asymmetric synthesis of l-proline regio- and stereoselectively labelled with deuterium
  作者：Makoto Oba、Tsutomu Terauchi、Akiko Miyakawa、Kozaburo Nishiyama

  DOI：10.1016/s0957-4166(99)00083-x

  日期：1999.3

  A synthesis of L-proline where all of the ring methylenes me stereoselectiveiy labelled with deuterium is described. A catalytic deuteration of protected 3,4-dehydro-L-proline using transition metal catalyst followed by RuO4-oxidation gave a [3,4-D-2]pyroglutamic acid derivative. A syn-selective deuteration of the aminal derived from the pyroglutamate with Et3SiD-BF3. OEt2 furnished (2S,3S,4R,5S)-[3,4,5-D-3]proline. The present procedure is also applied to the synthesis of the corresponding (2S,3S,4R,SR)-isomer. (C) 1999 Elsevier Science Ltd. All rights reserved.