DMTrOTpT | 7177-84-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: DMTrOTpT
• 英文别名: thymidylyl-(5'->3')-O^5'-(4,4'-dimethoxy-trityl)-thymidine；5'-O-(Di-p-methoxy-trityl)-thymidylyl-(3'->5')-thymidin；5'-O-Di-(p-methoxytrityl)-thymidyl-(3'->5')-thymidin；[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• CAS: 7177-84-6
• 化学式: C₄₁H₄₅N₄O₁₄P
• 分子量: 848.8
• InChiKey: NRHRFDFHTTWCBH-UWNKZCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  221
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  DMTrOTpT 生成 胸苷酰(3'->5')胸苷铵盐
  参考文献：
  名称：

  HAMAMOTO, SHOJI;SHISHIDO, NOBUYOSHI;TAKAKU, HIROSHI, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+

  摘要：

  DOI：
• 作为产物：
  描述：

  保护胸苷 在 N-甲基咪唑 、 sodium hydroxide 、 喹啉-8-磺酰氯 、 三乙胺 、 碘甲烷 、 4-硝基苯甲醛肟 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 反应 14.0h， 生成 DMTrOTpT
  参考文献：
  名称：

  2-(2-吡啶基)乙基基团作为寡核苷酸合成中新的核苷酸间磷酸盐保护基团的用途

  摘要：

  2-(2-吡啶基)乙基用作核苷酸间磷酸酯的高选择性保护基团，可在温和条件下通过在 CH3CN 中用 CH3I 处理去除，而不会发生 N-烷基化等副反应。

  DOI：

  10.1246/cl.1986.699

文献信息

• 2-mercaptobenzothiazole--an improved reagent for the removal of methyl phosphate protecting groups from oligodeoxynucleotide phosphotriesters.
  作者：Alex Andrus、Serge L. Beaucage

  DOI：10.1016/s0040-4039(00)80791-1

  日期：1988.1

  An equimolar (1.5M) solution of 2-mercaptobenzothiazole and N,N-diisopropylethylamine in 1-methyl-2-pyrrolidinone efficiently removed the methyl phosphate protecting groups from deoxynucleotide phosphotriesters and yielded synthetic oligomers of high genetic integrity. This odorless reagent can therefore substitute for hazardous thiophenol usually used for this purpose.

  2-巯基苯并噻唑和N，N-二异丙基乙胺在1-甲基-2-吡咯烷酮中的等摩尔（1.5M）溶液可有效地从脱氧核苷酸磷酸三酯中除去磷酸甲基保护基，并获得具有高遗传完整性的合成低聚物。因此，这种无味的试剂可以代替通常用于此目的的有害苯硫酚。
• USE OF 2-(2-PYRIDYL)ETHYL GROUP AS A NEW PROTECTING GROUP OF INTERNUCLEOTIDIC PHOSPHATES IN OLIGONUCLEOTIDE SYNTHESIS
  作者：Hiroshi Takaku、Shoji Hamamoto、Testuo Watanabe

  DOI：10.1246/cl.1986.699

  日期：1986.5.5

  2-(2-Pyridyl)ethyl group is used as a highly selective protecting group of internucleotidic phosphates that is removable under mild conditions by treatment with CH3I in CH3CN without a side reaction such as N-alkylation.

  2-(2-吡啶基)乙基用作核苷酸间磷酸酯的高选择性保护基团，可在温和条件下通过在 CH3CN 中用 CH3I 处理去除，而不会发生 N-烷基化等副反应。
• Large-Scale Synthesis of Oligonucleotide Phosphorothioates Using 3-Amino-1,2,4-dithiazole-5-thione as an Efficient Sulfur-Transfer Reagent
  作者：Jin-Yan Tang、Yongxin Han、Jimmy X. Tang、Zhaoda Zhang

  DOI：10.1021/op990092g

  日期：2000.5.1

  solid-phase synthesis of oligonucleotide phosphorothioates via the phosphoramidite method. The efficiency of ADTT was investigated by solid-phase syntheses of dinucleotide and oligonucleotide phosphorothioates. The results show that ADTT is a highly efficient sulfur-transfer reagent and fully compatible with automated solid-phase synthesis. ADTT has been applied in manufacture of oligonucleotide phosphorothioates

  一种市售且廉价的化合物 3-氨基-1,2,4-二噻唑-5-硫酮 (ADTT) 被发现是一种新的硫转移试剂，用于通过亚磷酰胺法固相合成寡核苷酸硫代磷酸酯。ADTT 的效率通过二核苷酸和寡核苷酸硫代磷酸酯的固相合成来研究。结果表明，ADTT是一种高效的硫转移试剂，与自动化固相合成完全兼容。ADTT已应用于寡核苷酸硫代磷酸酯的生产，以显着降低成本。
• Kamaike, Kazuo; Ueda, Souichi; Tsuchiya, Hiromichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 8, p. 2928 - 2931
  作者：Kamaike, Kazuo、Ueda, Souichi、Tsuchiya, Hiromichi、Takaku, Hiroshi

  DOI：——

  日期：——
• ——
  作者：Masatoshi Ushioda、Michinori Kadokura、Tomohisa Moriguchi、Akio Kobori、Morihiro Aoyagi、Kohji Seio、Mitsuo Sekine

  DOI：10.1002/1522-2675(200209)85:9<2930::aid-hlca2930>3.0.co;2-2

  日期：2002.9

  In connection with the synthesis of guanosine-capped of oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleoticles having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5'-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr(2))OEt 42 with a simpler model compound. methyl phosphorimidazolide 34. in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxyriucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.