3'-O-(p,p'-dimethoxytrityl)thymidine 5'-(allyl N,N-diisopropylphosphoramidite) | 215318-35-7

• 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: 3'-O-(p,p'-dimethoxytrityl)thymidine 5'-(allyl N,N-diisopropylphosphoramidite)
• 英文别名: 3'-O-p,p'-dimethoxytritylthymidine 5'-(allyl N,N-diisopropylphosphoramidite)；1-[(2R,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[[[di(propan-2-yl)amino]-prop-2-enoxyphosphanyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 215318-35-7
• 化学式: C₄₀H₅₀N₃O₈P
• 分子量: 731.826
• InChiKey: PIXLOLLZIAXAON-SIHXTDFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-(p,p'-dimethoxytrityl)thymidine 5'-(allyl N,N-diisopropylphosphoramidite) 在 四氮唑 、 邻苯二甲酸二甲酯 、 ethylmethyldioxirane 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-cyanooxolan-3-yl] [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl prop-2-enyl phosphate
  参考文献：
  名称：

  Ethyl(methyl)dioxirane as an Efficient Reagent for the Oxidation of Nucleoside Phosphites into Phosphates under Nonbasic Anhydrous Conditions

  摘要：

  [GRAPHICS]A convenient method for the oxidation of nucleoside phosphites into phosphates under nonbasic and nonaqueous conditions using commercially available ethyl(methyl)dioxirane has been developed. This oxidation is effective with both N-protected and N-unprotected strategies.

  DOI：

  10.1021/ol000364w
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 吡啶 、 二异丙基铵盐四氮唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 31.0h， 生成 3'-O-(p,p'-dimethoxytrityl)thymidine 5'-(allyl N,N-diisopropylphosphoramidite) 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  一种通过亚磷酰胺保护的亚磷酰胺方法，在3'-末端带有磷酸酯的寡脱氧核糖核苷酸的新方法：碱基不稳定的核苷酸-氨基酸和-肽结合物的有效合成

  摘要：

  开发了一种新的通过烯丙基保护的亚磷酰胺法合成3'-端磷酸化DNA低聚物的新方法。此方法对于制备具有碱基不稳定结构的衍生物（例如oligoDNA-OPO（OH）OCH 2 CH（R）Z ）特别有用，其中Z是吸电子功能。例如，寡核苷酸-氨基酸偶联物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（NH 2）COOH，和一个寡核苷酸-肽缀合物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（已获得高纯度的NH 2 COOH。

  DOI：

  10.1016/s0040-4039(99)00748-0

文献信息

• A Novel Synthesis of Oligonucleotide–Peptide Conjugates with a Base-Labile Phosphate Linker between the Two Components According to the Allyl-Protected Phosphoramidite Strategy
  作者：Akira Sakakura、Yoshihiro Hayakawa

  DOI：10.1016/s0040-4020(00)00376-8

  日期：2000.6

  the hydroxyl of a serine or threonine residue of a peptide by a phosphodiester bond. This synthesis utilizes the phosphoramidite method with allyl for the phosphate linkages and the C-terminal of the peptide and allyloxycarbonyl for the nucleoside bases and the N-terminal of the peptide. In this synthesis, the removal of the allylic protecting groups and the detachment of the products was achieved under

  已经完成了对碱基不稳定的核苷酸-肽结合物的有效合成，其中两个组分通过磷酸二酯键直接连接在核苷酸的末端羟基和肽的丝氨酸或苏氨酸残基的羟基之间。该合成利用亚磷酰胺方法，其中烯丙基用于肽的磷酸键和C-末端，烯丙氧基羰基用于肽的核苷碱基和N-末端。在该合成中，在非碱性或温和的碱性条件下实现了烯丙基保护基的去除和产物的分离，从而使不稳定的磷酸酯连接基不引起明显的分解，因此以高纯度获得了目标缀合物。高产。
• A FACILE SYNTHESIS OF 5′-END SOLID-ANCHORED, 3′-END FREE OLIGODEOXYRIBONUCLEOTIDES VIA THE (5′ → 3′)-ELONGATED PHOSPHORAMIDITE STRATEGY
  作者：Akira Sakakura、Yoshihiro Hayakawa

  DOI：10.1081/ncn-100002082

  日期：2001.2.28

  It is demonstrated that not only N-2- but also O-6-protection of the guanine base is necessary for obtaining the oligodeoxyribonucleotides in high yields and at a high purity in the solid-phase synthesis via the (5 ' --> 3 ')-chain elongated phosphoramidite approach.
• Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation
  作者：Yoshihiro Hayakawa、Rie Kawai、Kaori Otsuki、Masanori Kataoka、Akira Matsuda

  DOI：10.1016/s0960-894x(98)00459-4

  日期：1998.9

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.