O-(二苯氧基磷酰)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酸 | 105751-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: O-(二苯氧基磷酰)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酸
• 英文名称: Boc-Ser(PO3Ph2)-OH
• 英文别名: Boc-O-diphenylphospho-L-serine；(2S)-3-diphenoxyphosphoryloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 105751-07-3
• 化学式: C₂₀H₂₄NO₈P
• 分子量: 437.386
• InChiKey: RBECNYYYUJDBGE-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  O-(二苯氧基磷酰)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 2.05h， 生成 tert-butyl N-[(2S)-3-diphenoxyphosphoryloxy-1-(methylamino)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  The synthesis of multiple O-phosphoseryl-containing peptides via phenyl phosphate protection

  摘要：

  DOI：

  10.1021/jo00252a041
• 作为产物：
  描述：

  氯磷酸二苯酯 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 O-(二苯氧基磷酰)-N-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酸
  参考文献：
  名称：

  Perich, John W.; Alewood, Paul F.; Johns, R. B., Australian Journal of Chemistry, 1991, vol. 44, # 2, p. 233 - 252

  摘要：

  DOI：

文献信息

• The efficient synthesis of a complex O-phosphoseryl-containing peptide Ac-Glu-PSer-Leu-PSer-P-Ser-PSer-Glu-Glu-NHMe
  作者：John W. Perich、R. B. Johns

  DOI：10.1039/c39880000664

  日期：——

  The title octapeptide was prepared by the synthesis of the fully protected tetra-Ser(PO3Ph2)-octapeptide by incorporation of Boc-Ser(PO3Ph2)-OH (Boc = t-butoxycarbonyl) in conventional Boc/solution phase peptide synthesis, followed by the complete hydrogenolytic cleavage of the phenyl groups from the Ser(PO3Ph2)-octapeptide.

  通过在常规Boc /溶液相中掺入Boc-Ser（PO 3 Ph 2）-OH（Boc =叔丁氧羰基）来合成完全保护的四-Ser （PO 3 Ph 2）-八肽，从而制备标题八肽肽合成，然后完全水解水解Ser（PO 3 Ph 2）-八肽中的苯基。
• Synthesis of Casein-Related Peptides and Phosphopeptides. XVI. The Efficient Synthesis of the Casein-Related O-Phosphoseryl-Containing Peptide Ac-Glu-Ser(P)-Leu-Ser(P)-Ser(P)-Ser(P)-Glu-Glu-NHMe
  作者：JW Perich、RB Johns、EC Reynolds

  DOI：10.1071/ch9920385

  日期：——

  The multiple-O-phosphoseryl-containing peptide, Ac-Glu-Ser (P)-Leu-Ser (P)-Ser (P)-Ser (P)-Glu-Glu-NHMe, was prepared in high yield by the use of Boc-Ser(PO3Ph2)-OH in the Boc mode of peptide synthesis for the preparation of the protected Ser(PO3Ph2)-octapeptide followed by its one-step hydrogenolytic deprotection with platinum oxide. Peptide synthesis was performed by the repetitive excess mixed-anhydride coupling procedure and 40% CF3CO2H/CH2Cl2 for removal of the Boc group from intermediate peptides. The phosphopeptide was found to be greater than 99% pure by C8 r.p.-h.p.1.c. analysis, and was readily characterized by amino acid analysis, 13C n.m.r. spectroscopy and f.a.b. mass spectrometry.

  利用 Boc-Ser(PO3Ph2)-OH 以 Boc 多肽合成模式制备受保护的 Ser(PO3Ph2)-八肽，然后用氧化铂进行一步氢解脱保护，高产制备了含多个 O-膦丝酰基的多肽 Ac-Glu-Ser(P)-Leu-Ser(P)-Ser(P)-Ser(P)-Glu-Glu-NHMe。肽的合成采用重复过量混合酸酐偶联程序和 40% CF3CO2H/CH2Cl2 去除中间肽上的 Boc 基团。通过 C8 r.p.-h.p.1.c.分析发现，磷酸肽的纯度超过 99%，并可通过氨基酸分析、13C n.m.r.光谱和 f.a.b. 质谱分析进行表征。
• A novel approach to phosphopeptide synthesis-preparation of glu-pser-leu
  作者：P.F. Alewood、J.W. Perich、R.B. Johns

  DOI：10.1016/s0040-4039(01)80081-2

  日期：1984.1
• A new approach to phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides
  作者：N. Mora、J.M. Lacombe、A.A. Pavia

  DOI：10.1016/s0040-4039(00)60441-0

  日期：1993.4

  Several phosphoserine and phosphothreonine synthons suitable for the stepwise synthesis of phosphopeptides have been prepared. Treatment of methylthiomethyl (MTM) esters of either benzyloxycarbonyl (Z), tert-butyloxycarbonyl (Boc) and allyloxycarbonyl (Alloc) serine and / or threonine with phosphochloridate in pyridine, followed by MgBr2 cleavage of MTM in diethylether, afforded the title compounds in excellent yields.
• An Efficient One-Pot Synthesis of<i>N</i>-Protected α-Amino-β-dialkoxyphosphinyloxy(diphenoxyphosphinyloxy)-carboxylic Acids (Phosphate-Group Esters of<i>O</i>-Phosphorylated<i>N</i>-Protected α-Amino-β-hydroxyamino Acids)
  作者：John W. Perich、Paul F. Alewood、R. B. Johns

  DOI：10.1055/s-1986-31710

  日期：——