chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane | 221325-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane
• 英文别名: Chloro-dimethyl-[2-(4-nitrophenyl)propan-2-yl]silane
• CAS: 221325-35-5
• 化学式: C₁₁H₁₆ClNO₂Si
• 分子量: 257.792
• InChiKey: OFLGMQIIZBPACY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane 在 咪唑 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 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：

  Alpha-(二甲基氯化硅烷)异丙苯 在 硝酸铵 、 氢氧化钾 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸酐 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane
  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

• A Facile Silyl Linker Strategy for the Solid-Phase Synthesis of Protected Glycopeptide: Synthesis of an N-Terminal Fragment of IL-2 (1–10)
  作者：Akira Ishii、Hironobu Hojo、Aki Kobayashi、Kazuhiko Nakamura、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4020(00)00588-3

  日期：2000.8

  An N-terminal glycodecapeptide fragment of interleukin 2 (1) was synthesized by solid-phase method utilizing a new silyl linker. The O-silylated Fmoc–Thr–OAll was attached to the commercial HMP-resin and peptide chain elongation was performed by Fmoc protocol to produce a protected heptapeptide (3–10), which was cleaved from the resin by fluoridolysis and used as the amino component for further condensation

  通过使用新的甲硅烷基接头的固相方法合成了白介素2（1）的N末端糖基肽片段。将O甲硅烷基化的Fmoc–Thr–OAll连接到商用HMP树脂上，并通过Fmoc方案进行肽链延伸，以生成受保护的七肽（3-10），该七肽通过氟解从树脂上裂解下来并用作氨基组分进一步固结在固体载体上。另一方面，Fmoc-Thr（GalNAc）-OAll衍生物的6-羟基被连接基甲硅烷基化并连接到树脂上。在树脂上进行了脱芳基作用，与七肽（3-10）的缩合反应以及在N末端带有两个氨基酸的延伸。氟离子介导的裂解释放N-和来自固体支持物的C-保护的糖肽具有良好的效率。完全脱保护的糖肽也通过树脂上的脱甲硅烷基化和硅烷基醚键的酸性裂解而合成。
• 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.