tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate | 220155-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate
• CAS: 220155-70-4
• 化学式: C₂₅H₂₄N₂O₆
• 分子量: 448.475
• InChiKey: RLFCFDFXZSSUEY-CJFMBICVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以61%的产率得到alpha-甲基-D-色氨酸
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8
• 作为产物：
  描述：

  salicylalanine 在 N,N-二甲基丙烯基脲 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 tert-butyl 3-[[(3R,10bR)-3-methyl-2,5-dioxo-10bH-[1,3]oxazolo[3,2-c][1,3]benzoxazin-3-yl]methyl]indole-1-carboxylate
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8

文献信息

• The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan
  作者：Murray Goodman、Jinfang Zhang、Peter Gantzel、Ettore Benedetti

  DOI：10.1016/s0040-4039(98)02302-8

  日期：1998.12

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.