5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine | 224157-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine
• 英文别名: TBDPS(-3)[TMS(-5)]2,6,7-deoxy-L-lyxOctf(a)-thymin-1-yl；1-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-[(1S)-4-hydroxy-1-trimethylsilyloxybutyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 224157-41-9
• 化学式: C₃₂H₄₆N₂O₆Si₂
• 分子量: 610.898
• InChiKey: HNUPBMCYJUSSCS-QUAHOIDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine 在 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以90%的产率得到5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(oxo-propan)-thymidine
  参考文献：
  名称：

  Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines

  摘要：

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00246-x
• 作为产物：
  描述：

  1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 在 sodium hydroxide 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 双氧水 、 六甲基二硅氮烷 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 9.25h， 生成 5'-O-(trimethylsilyl), 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(propan-1-ol)-thymidine
  参考文献：
  名称：

  Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines

  摘要：

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00246-x

文献信息

• Synthesis of Phostone-Constrained Nucleic Acid (P-CNA) Dinucleotides Through Intramolecular Arbuzov's Reaction
  作者：Dan-Andrei Catana、Marie Maturano、Corinne Payrastre、Pierre Lavedan、Nathalie Tarrat、Jean-Marc Escudier

  DOI：10.1002/ejoc.201101061

  日期：2011.12

  P-CNAs are dinucleotide building blocks in which the torsional angles α and β of the sugar/phosphate backbone are constrained to non-canonical values within a cyclic phosphonate structure (phostone) synthesised by diastereoselective intramolecular Arbuzov reaction. The reaction has been improved through the use of microwave activation and addition of lithium bromide.

  P-CNA 是二核苷酸结构单元，其中糖/磷酸盐骨架的扭转角 α 和 β 被限制为非对映选择性分子内 Arbuzov 反应合成的环状膦酸酯结构（膦）内的非规范值。通过使用微波活化和添加溴化锂，该反应得到了改进。
• 5′-C-Tosyloxyalkylnucleosides. Models for Oligonucleotide Coupling with Nucleophiles
  作者：V. Banuls、V. Sarramegna、C. Froment、J M. Escudier、L. Gorrichon

  DOI：10.1080/07328319908044777

  日期：1999.6

  5'-C-substituted nucleosides with an hydroxyalkyl chain are synthesized. The stereochemistry of the new stereogenic center is defined. After introduction of a tosyl group, dimer models are prepared to evaluate the conjugation with amines used as nucleophiles.
• Allylsilanes in the preparation of 5′-C-hydroxy or bromo alkylthymidines
  作者：Valérie Banuls、Jean-Marc Escudier

  DOI：10.1016/s0040-4020(99)00246-x

  日期：1999.4

  The reaction of 5'-C-thymidine aldehyde with allytrimethylsilane promoted by BF3:Et2O lead stereoselectively to 5'-C(S)-allylthymidine which is converted to 5'-C(S) C(S)-hydroxyhexylthymidine. 5'-C-(R or S) hydroxypentylthymidine can be obtained by using omega-tertButyldimethylsilyloxyallyltrimethylsilane in the Sakurai reaction. In the same conditions, omega-Bromoallyltrimethylsilane adds to the aldehyde with a complete transposition of the siliranium intermediate and allows the preparation of the 5'-C(S)-bromopentene derivative, (C) 1999 Elsevier Science Ltd. All rights reserved.