N-(tert-butoxycarbonyl)amino-ethane-sulfinylchloride | 134019-74-2

• 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: N-(tert-butoxycarbonyl)amino-ethane-sulfinylchloride
• 英文别名: 1,1-Dimethylethyl N-[2-(chlorosulfinyl)ethyl]carbamate；tert-butyl N-(2-chlorosulfinylethyl)carbamate
• CAS: 134019-74-2
• 化学式: C₇H₁₄ClNO₃S
• 分子量: 227.712
• InChiKey: ZOPAWOFHICHISW-UHFFFAOYSA-N

物化性质

• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)amino-ethane-sulfinylchloride 在 ruthenium trichloride N-甲基吗啉 、 sodium periodate 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 N-(tert-butyloxycarbonyl)amino-2-phenyl-ethane-sulfinyl-prolinyl-isoleucine-methylamide
  参考文献：
  名称：

  Synthesis of peptides containing a sulfinamide or a sulfonamide transition-state isostere

  摘要：

  A versatile synthesis of peptides incorporating the sulfonamide or sulfonamide transition-state analogue is described. Apart from the easily accessible Gly-Xxx isosteres used as haptens to elicit catalytic antibodies, other amino acids than Gly can be prepared by alpha-alkylation of the sulfonamide containing peptides. This is illustrated with the synthesis of a potential HIV-protease inhibitor 27.

  DOI：

  10.1016/s0040-4020(01)86293-1
• 作为产物：
  描述：

  二-叔丁氧羰基-胱胺 在 乙酸酐 、 氯 作用下， 生成 N-(tert-butoxycarbonyl)amino-ethane-sulfinylchloride
  参考文献：
  名称：

  含有亚磺酰胺或磺酰胺部分的肽：新的过渡态类似物

  摘要：

  描述了酰胺键水解的两种新型过渡态类似物的通用合成：亚磺酰胺和磺酰胺部分。这些过渡态类似物是肽的一部分，将用于产生催化抗体以及开发蛋白酶抑制剂。

  DOI：

  10.1016/s0040-4039(00)92641-8

文献信息

• Synthesis and evaluation of chloromethyl sulfoxides as a new class of selective irreversible cysteine protease inhibitors
  作者：Arwin J. Brouwer、Anton Bunschoten、Rob M.J. Liskamp

  DOI：10.1016/j.bmc.2007.07.045

  日期：2007.11

  The synthesis and biological evaluation of a new class of selective irreversible cysteine protease inhibitors is described. A set of amino acid based chloromethyl sulfoxides was prepared and they were found to inhibit irreversibly the cysteine protease papain. They were selective for cysteine proteases since no inhibition was found for the serine protease chymotrypsin.

  描述了新型的选择性不可逆半胱氨酸蛋白酶抑制剂的合成和生物学评估。制备了一套基于氨基酸的氯甲基亚砜，发现它们不可逆地抑制半胱氨酸蛋白酶木瓜蛋白酶。由于对丝氨酸蛋白酶胰凝乳蛋白酶没有抑制作用，因此它们对半胱氨酸蛋白酶具有选择性。
• Synthetic receptors based on peptidosulfonamide peptidomimetics
  作者：Dennis W.P.M. Löwik、Suzanne J.E. Mulders、Yuan Cheng、Yuefei Shao、Rob M.J. Liskamp

  DOI：10.1016/0040-4039(96)01882-5

  日期：1996.11

  We have synthesized tweezer-like receptor molecules based on peptidosulfonamide peptidomimetics. These compounds were screened for binding against a ∼25,000 member encoded tripeptide library. One of these synthetic receptors showed a remarkable binding selectivity.

  我们已经合成了基于肽磺酰胺拟肽的镊子样受体分子。筛选这些化合物与约25,000个成员编码的三肽文库的结合。这些合成受体之一显示出显着的结合选择性。
• Molecular diversity of peptidomimetics: Approaches to the solid-phase synthesis of peptidosulfonamides
  作者：Dries B.A. de Bont、Wilna J. Moree、Rob M.J. Liskamp

  DOI：10.1016/0968-0896(96)00061-2

  日期：1996.5

  In order to use the potential molecular diversity of the peptidosulfonamide peptidomimetics ultimately in libraries, approaches towards the solid-phase synthesis of peptidosulfonamides are a prerequisite. It is shown that peptidosulfonamides can be synthesized by solid-phase synthesis methods using either a Merrifield or a Tentagel(R) resin. Better and more reproducible results are obtained using the latter resin. The possibility to prepare cyclic peptidosulfonamides was illustrated by the synthesis of cyclo-phenylalanyl Psi [CH2S(O)(2)N]-glycine. However, translation of synthesis of peptidosulfonamides in solution to a solid-phase method was rather laborious and still requires careful optimization. Copyright (C) 1996 Elsevier Science Ltd.
• [EN] COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：FOGHORN THERAPEUTICS INC

  公开号：WO2020160180A1

  公开（公告）日：2020-08-06

  The present disclosure features compounds useful for the treatment of BAF complex-related disorders.