N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine benzyl ester | 171820-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine benzyl ester
• 英文别名: benzyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxypropanoate
• CAS: 171820-92-1
• 化学式: C₄₄H₃₇NO₅
• 分子量: 659.781
• InChiKey: MOPRNJGDAVZOPS-RWYGWLOXSA-N

物化性质

• 沸点：
  808.2±65.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine benzyl ester 在 vanadyl trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以85%的产率得到Fmoc-O-苄基-L-丝氨酸
  参考文献：
  名称：

  Removal of Acid-Labile Protecting Groups on Carbohydrates Using Water-Tolerant and Recoverable Vanadyl Triflate Catalyst

  摘要：

  Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.

  DOI：

  10.1021/jo061881g
• 作为产物：
  描述：

  L-丝氨酸苄酯盐酸盐 在 sodium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 39.08h， 生成 N-9-fluorenylmethoxycarbonyl-O-trityl-L-serine benzyl ester
  参考文献：
  名称：

  Direct glycosylation of protected O-tritylserine esters and oligopeptides

  摘要：

  N-Finoc-3-O-Tr-L-serine methyl and benzyl esters, as well as a tripeptide FmocAlaSeI(Tr)GlyOBn were directly glycosylated by 3,4,6-tri-O-acetyl-1,2-O-(1-cyanoethylidene)-alpha-D-galactopyranose in the presence of TrClO(4) in dichloromethane, yielding 32-57% of N-Fmoc-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-L-serine esters and the corresponding tripeptide.

  DOI：

  10.1016/0008-6215(95)00097-d

文献信息

• Development of oxetane modified building blocks for peptide synthesis
  作者：Stefan Roesner、Jonathan D. Beadle、Leo K. B. Tam、Ina Wilkening、Guy J. Clarkson、Piotr Raubo、Michael Shipman

  DOI：10.1039/d0ob01208d

  日期：——

  The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported. The preparation of building blocks containing non-glycine residues at the N-terminus in a stereochemically controlled manner is challenging. Here, a practical 4-step route to such building blocks is demonstrated, through the synthesis of dipeptides containing contiguous

  报道了在溶液和固相肽合成（SPPS）中氧杂环丁烷修饰的二肽结构单元的合成和使用。以立体化学控制的方式制备在N端含有非甘氨酸残基的结构单元是具有挑战性的。在此，通过合成包含连续丙氨酸残基的二肽，证明了通向此类结构单元的实际4步路线。这些新衍生物在包含18个氨基酸的富含丙氨酸的肽序列的骨架的特定位点上的掺入通过固相肽合成。另外，通过改变合成路线（对于Cys和Met）和改变保护基的策略（对于His，Ser和Thr），报道了使所有20个蛋白原氨基酸都可以掺入这种二肽构件的新方法。 ）。
• Removal of Acid-Labile Protecting Groups on Carbohydrates Using Water-Tolerant and Recoverable Vanadyl Triflate Catalyst
  作者：Ming-Chung Yan、Yeng-Nan Chen、Huan-Ting Wu、Chang-Ching Lin、Chien-Tien Chen、Chun-Cheng Lin

  DOI：10.1021/jo061881g

  日期：2007.1.1

  Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.
• Direct glycosylation of protected O-tritylserine esters and oligopeptides
  作者：Andrzej Rajca、Manfred Wiessler

  DOI：10.1016/0008-6215(95)00097-d

  日期：1995.9

  N-Finoc-3-O-Tr-L-serine methyl and benzyl esters, as well as a tripeptide FmocAlaSeI(Tr)GlyOBn were directly glycosylated by 3,4,6-tri-O-acetyl-1,2-O-(1-cyanoethylidene)-alpha-D-galactopyranose in the presence of TrClO(4) in dichloromethane, yielding 32-57% of N-Fmoc-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-L-serine esters and the corresponding tripeptide.