tert-butyl ((1R,2R)-3-hydroxy-1-phenyl-1-selenocyanatopropan-2-yl)carbamate | 1377320-85-8

• 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: tert-butyl ((1R,2R)-3-hydroxy-1-phenyl-1-selenocyanatopropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(1R,2R)-3-hydroxy-1-phenyl-1-selenocyanatopropan-2-yl]carbamate
• CAS: 1377320-85-8
• 化学式: C₁₅H₂₀N₂O₃Se
• 分子量: 355.295
• InChiKey: KXARSRIMKKGKDW-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((1R,2R)-3-hydroxy-1-phenyl-1-selenocyanatopropan-2-yl)carbamate 在 sodium tetrahydroborate 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry

  摘要：

  An efficient synthetic route to a suitably protected beta-selenol-phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

  DOI：

  10.1021/ol3012265
• 作为产物：
  描述：

  (R)-tert-butyl 2,2-dimethyl-4-((R)-phenyl(selenocyanato)methyl)oxazolidine-3-carboxylate 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以75%的产率得到tert-butyl ((1R,2R)-3-hydroxy-1-phenyl-1-selenocyanatopropan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and Utility of β-Selenol-Phenylalanine for Native Chemical Ligation–Deselenization Chemistry

  摘要：

  An efficient synthetic route to a suitably protected beta-selenol-phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

  DOI：

  10.1021/ol3012265

文献信息

• Synthesis and Utility of β-Selenophenylalanine and β-Selenoleucine in Diselenide–Selenoester Ligation
  作者：Xiaoyi Wang、Leo Corcilius、Bhavesh Premdjee、Richard J. Payne

  DOI：10.1021/acs.joc.9b02665

  日期：2020.2.7

  The synthesis of suitably protected beta-selenophenylalanine and beta-selenoleucine amino acids was accomplished from Garner's aldehyde as a common starting point. These selenoamino acids were incorporated into model peptides and shown to facilitate rapid diselenide-selenoester ligation (DSL) with peptide selenoesters which, when coupled with in situ deselenization, afforded native peptide products. The utility of one-pot DSL-deselenization chemistry at phenylalanine and leucine was demonstrated through the rapid synthesis of a glycosylated interferon-gamma fragment and the chemokine-binding protein UL22A, respectively.