tert-butyl (1S,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate | 528523-45-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl (1S,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate
• 英文别名: tert-butyl ((1S,2S)-3-((tert-butyldiphenylsilyl)oxy)-1-hydroxy-1-phenylpropan-2-yl)carbamate；tert-butyl N-[(1S,2S)-3-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-1-phenylpropan-2-yl]carbamate
• CAS: 528523-45-7
• 化学式: C₃₀H₃₉NO₄Si
• 分子量: 505.729
• InChiKey: MTZULFARRVIPAT-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate 在 盐酸 、 四丁基氟化铵 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 生成 L-threo-2-amino-3-morpholino-1-phenylpropan-1-ol
  参考文献：
  名称：

  Practical Synthesis of threo-(S,2S)- and erythro-(1R,2S)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from l-Serine

  摘要：

  L-苏型和 d-赤型-1-苯基-2-棕榈酰氨基-3-吗啉代-1-丙醇 (PPMP) 都是由 L-丝氨酸立体选择性合成的。

  DOI：

  10.1055/s-1998-3132
• 作为产物：
  描述：

  (1S,2S)-(+)-2-氨基-1-苯基-1,3-丙二醇 在 咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 tert-butyl (1S,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate
  参考文献：
  名称：

  Synthesis of non-competitive inhibitors of Sphingomyelinases with significant activity

  摘要：

  A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino, moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00888-0

文献信息

• Nonhydrolyzable d‑phenylalanine-benzoxazole derivatives retain antitubercular activity
  作者：Michael J. Pepi、Shibin Chacko、Nicole Kopetz、Helena I.M. Boshoff、Gregory D. Cuny、Lizbeth Hedstrom

  DOI：10.1016/j.bmcl.2022.129116

  日期：2023.1

  emergence of drug resistant Mycobacterium tuberculosis, the causative agent of tuberculosis, demands the development of new drugs and new drug targets. We have recently reported that the d-phenylalanine benzoxazole Q112 has potent antibacterial activity against this pathogen with a distinct mechanism of action from other antimycobacterial agents. Q112 and previously reported derivatives were unstable in

  结核病的病原体——耐药结核分枝杆菌的出现，需要开发新药和新的药物靶点。我们最近报道， d-苯丙氨酸苯并恶唑Q112对这种病原体具有有效的抗菌活性，其作用机制与其他抗分枝杆菌药物不同。 Q112和之前报道的衍生物在血浆中不稳定，没有观察到游离化合物。在这里，我们扩展了抗分枝杆菌活性的结构-活性关系，并发现了血浆结合减少的不可水解衍生物。我们还表明，抗菌活性和对 PanG 的抑制之间不存在相关性，PanG 是这些化合物的假定靶点。
• Practical Synthesis of <i>threo</i>-(<i>S</i>,2<i>S</i>)- and <i>erythro</i>-(1<i>R</i>,2<i>S</i>)-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from l-Serine
  作者：Atsushi Nishida、Hiroshi Sorimachi、Mie Iwaida、Miyako Matsumizu、Tomohiko Kawate、Masako Nakagawa

  DOI：10.1055/s-1998-3132

  日期：1998.4

  Both l-threo- and d-erythro-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) were synthesized stereoselectively from l-serine.

  L-苏型和 d-赤型-1-苯基-2-棕榈酰氨基-3-吗啉代-1-丙醇 (PPMP) 都是由 L-丝氨酸立体选择性合成的。
• Synthesis of non-competitive inhibitors of Sphingomyelinases with significant activity
  作者：Tsutomu Yokomatsu、Tetsuo Murano、Takeshi Akiyama、Junichi Koizumi、Shiroshi Shibuya、Yoshiaki Tsuji、Shinji Soeda、Hiroshi Shimeno

  DOI：10.1016/s0960-894x(02)00888-0

  日期：2003.1

  A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino, moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase. (C) 2002 Elsevier Science Ltd. All rights reserved.