tert-butyl (S)-1-isothiocyanato-3-methylbutan-2-ylcarbamate | 1172596-80-3

• 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: tert-butyl (S)-1-isothiocyanato-3-methylbutan-2-ylcarbamate
• 英文别名: Boc-Val-ψ[CH2NCS]；tert-butyl N-[(2S)-1-isothiocyanato-3-methylbutan-2-yl]carbamate
• CAS: 1172596-80-3
• 化学式: C₁₁H₂₀N₂O₂S
• 分子量: 244.358
• InChiKey: GOXUNTZNFCYIDS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-1-isothiocyanato-3-methylbutan-2-ylcarbamate 、 N-benzyloxycarbonyl-L-phenylalanine hydrazide 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

  摘要：

  Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.004
• 作为产物：
  描述：

  二硫化碳 、 2-甲基-2-丙基[(2S)-1-氨基-3-甲基-2-丁烷基]氨基甲酸酯 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到tert-butyl (S)-1-isothiocyanato-3-methylbutan-2-ylcarbamate
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

  DOI：

  10.1021/jo900675s