N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl]-L-serine allyl ester | 221325-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl]-L-serine allyl ester
• 英文别名: prop-2-enyl (2S)-3-[dimethyl-[2-(4-nitrophenyl)propan-2-yl]silyl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 221325-37-7
• 化学式: C₃₂H₃₆N₂O₇Si
• 分子量: 588.733
• InChiKey: CYKXGUDBZTVXKK-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl]-L-serine allyl ester 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以88%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[(4-amino-α,α-dimethylbenzyl)dimethylsilyl]-L-serine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 、 chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane 在 N-甲基吗啉 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 以97%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl]-L-serine allyl ester
  参考文献：
  名称：

  A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

  摘要：

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00649-3

文献信息

• Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides
  作者：Kazuhiko Nakamura、Noriyasu Hanai、Masayuki Kanno、Aki Kobayashi、Yuki Ohnishi、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(98)02390-9

  日期：1999.1

  A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p-nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation or Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.