N^α-benzyloxycarbonyl-N^δ-(2-nitrobenzenesulfonyl)-L-ornithine tert-butyl ester | 370579-56-9

• 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^α-benzyloxycarbonyl-N^δ-(2-nitrobenzenesulfonyl)-L-ornithine tert-butyl ester
• 英文别名: tert-butyl (2S)-5-[(2-nitrophenyl)sulfonylamino]-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 370579-56-9
• 化学式: C₂₃H₂₉N₃O₈S
• 分子量: 507.565
• InChiKey: PSDZOKBGQOCTRB-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 N^α-benzyloxycarbonyl-N^δ-(2-nitrobenzenesulfonyl)-L-ornithine tert-butyl ester 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到tert-butyl (2S)-5-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl-(2-nitrophenyl)sulfonylamino]-2-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  Synthesis of novel amino acid carbohydrate hybrids via Mitsunobu glycosylation of nitrobenzenesulfonamides

  摘要：

  Amino acid derived 2-nitrobenzenesulfonamides were successfully condensed under Mitsunobu conditions with the primary alcohol of various saccharide and nucleoside derivatives to furnish the fully protected hybrids in excellent yield. One such hybrid was incorporated into a short peptide sequence in good overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01062-0
• 作为产物：
  描述：

  (S)-2-Benzyloxycarbonylamino-5-(2-nitro-benzenesulfonylamino)-pentanoic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N^α-benzyloxycarbonyl-N^δ-(2-nitrobenzenesulfonyl)-L-ornithine tert-butyl ester
  参考文献：
  名称：

  Synthesis of novel amino acid carbohydrate hybrids via Mitsunobu glycosylation of nitrobenzenesulfonamides

  摘要：

  Amino acid derived 2-nitrobenzenesulfonamides were successfully condensed under Mitsunobu conditions with the primary alcohol of various saccharide and nucleoside derivatives to furnish the fully protected hybrids in excellent yield. One such hybrid was incorporated into a short peptide sequence in good overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01062-0

文献信息

• Synthesis of novel amino acid carbohydrate hybrids via Mitsunobu glycosylation of nitrobenzenesulfonamides
  作者：John J. Turner、Dmitri V. Filippov、Mark Overhand、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4039(01)01062-0

  日期：2001.8

  Amino acid derived 2-nitrobenzenesulfonamides were successfully condensed under Mitsunobu conditions with the primary alcohol of various saccharide and nucleoside derivatives to furnish the fully protected hybrids in excellent yield. One such hybrid was incorporated into a short peptide sequence in good overall yield. (C) 2001 Elsevier Science Ltd. All rights reserved.