Fmoc-Asp(F)-O-t-Bu | 144156-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Asp(F)-O-t-Bu
• 英文别名: tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-fluoro-4-oxobutanoate
• CAS: 144156-44-5
• 化学式: C₂₃H₂₄FNO₅
• 分子量: 413.446
• InChiKey: FPQPXQVBXHAEBO-IBGZPJMESA-N

物化性质

• 沸点：
  585.8±50.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-Asp(F)-O-t-Bu 在 Lindlar's catalyst 甲氧基三甲基硅烷 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 N-(9-芴甲氧羰基)-N’-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-beta-D-吡喃葡萄糖基)-L-天冬酰胺
  参考文献：
  名称：

  Amino acid fluoride for glycopeptide synthesis

  摘要：

  The formation of N-glycosidic linkage between N-acetylglucosamine (GlcNAc) and asparagine (Asn) was effected using aspartic acid gamma-fluoride in combination with either glycosyl azide or silyl carbamate, by the action of Lindlar catalyst or Bu4NF Further elongation of peptide chain was performed to give pentapeptide. This method was further applied into the synthesis of trisaccharidic asparagine, using beta-methoxybenzyl assisted stereoselective B-mannosylation as the key transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02228-5
• 作为产物：
  描述：

  芴甲氧羰基-L-天冬氨酸-1-叔丁酯 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 以73.2%的产率得到Fmoc-Asp(F)-O-t-Bu
  参考文献：
  名称：

  Protected .beta.- and .gamma.-aspartic and -glutamic acid fluorides

  摘要：

  DOI：

  10.1021/jo00049a065

文献信息

• Synthesis of N-Linked Glycosyl Asparagine Derivatives with Unprotected Sugar Components
  作者：Akihiro Ishiwata、Maki Takatani、Yoshiaki Nakahara、Yukishige Ito

  DOI：10.1055/s-2002-22716

  日期：——

  A general methodology for the efficient formation of N-glycosidic linkage to asparagine (Asn), which, does not require the protection of sugar component hydroxyl groups is described. Aspartic acid fluoride was used in combination with N-allyloxycarbonyl (Alloc) glycosyl amines. Pd(0)-PhSiH3 mediated in situ Alloc removal-coupling was performed in aqueous solution dioxane to give Asn-linked carbohydrates in high yield.

  本文介绍了一种有效形成天冬酰胺（Asn）N-糖苷键的通用方法，该方法无需保护糖成分羟基。天冬氨酸氟化物与 N-烯丙氧羰基（Alloc）糖基胺结合使用。在二噁烷水溶液中进行了 Pd(0)-PhSiH3 介导的原位 Alloc 脱除-偶联反应，得到了高产率的 Asn 链接碳水化合物。
• Synthesis of asparagine-linked bacillosamine
  作者：Mohammed Nurul Amin、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.carres.2006.04.031

  日期：2006.8

  Various types of protein glycosylation have been identified from prokaryotes. Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium, Campylobacter jejuni. The structure of this glycan is unique, consisting of 5 Ga1NAc and 1 G1c, in addition to 2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose (bacillosamine; Bac), which is N-glycosidically linked to the side chain of asparagine (Asn). We synthesized Bac from a 2-azido-2-deoxy-D-galactose derivative, which was further converted to the Asn-linked form. (c) 2006 Published by Elsevier Ltd.
• Amino acid fluoride for glycopeptide synthesis
  作者：Yukishige Ito、Manfred Gerz、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(99)02228-5

  日期：2000.2

  The formation of N-glycosidic linkage between N-acetylglucosamine (GlcNAc) and asparagine (Asn) was effected using aspartic acid gamma-fluoride in combination with either glycosyl azide or silyl carbamate, by the action of Lindlar catalyst or Bu4NF Further elongation of peptide chain was performed to give pentapeptide. This method was further applied into the synthesis of trisaccharidic asparagine, using beta-methoxybenzyl assisted stereoselective B-mannosylation as the key transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Protected .beta.- and .gamma.-aspartic and -glutamic acid fluorides
  作者：Louis A. Carpino、El Sayed M. E. Mansour

  DOI：10.1021/jo00049a065

  日期：1992.11