2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester | 290292-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester
• 英文别名: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-(D)-pentanoic acid tert-butyl ester；tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodopentanoate
• CAS: 290292-99-8
• 化学式: C₂₄H₂₈INO₄
• 分子量: 521.395
• InChiKey: ZUPUMAIRSUEDLA-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester 在 三乙胺 作用下， 反应 4.0h， 以90%的产率得到tert-butyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate
  参考文献：
  名称：

  Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

  摘要：

  Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

  DOI：

  10.1021/ol503664t
• 作为产物：
  描述：

  N-(9-芴甲氧羰基)-D-谷氨酸 1-叔丁酯 在 N-甲基吗啉 、 咪唑 、 碘 、 三苯基膦 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 生成 2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-iodo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

  摘要：

  Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

  DOI：

  10.1021/ol503664t

文献信息

• Solid-Phase Synthesis of New <i>S</i>-Glycoamino Acid Building Blocks
  作者：Laurence Jobron、Gerd Hummel

  DOI：10.1021/ol006019o

  日期：2000.7.1

  [GRAPHICS]Efficient synthesis of unprotected S-glycoamino acid building blocks in the solid phase by coupling a sugar 1-thiolate with iodine activated fluoren-9-ylmethoxycarbonyl (Fmoc) protected amino acids.