1-((2R,3R,4R,5R)-3,4-Bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one | 127838-69-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-((2R,3R,4R,5R)-3,4-Bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
• 英文别名: 1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
• CAS: 127838-69-1
• 化学式: C₂₇H₅₄N₂O₅SSi₃
• 分子量: 603.059
• InChiKey: SNIWSGAYWNOCEI-JMJGKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4R,5R)-3,4-Bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 在 selenium 、 sodium tetrahydroborate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 2′-O-tert-butyldimethylsilyl-3′,5′-O-(di-tert-butylsilanediyl)-2-selenouridine
  参考文献：
  名称：

  An Efficient Synthesis of 2-Selenouridine and Its Phosphoramidite Precursor

  摘要：

  We describe an efficient and scalable synthetic route to the natural occurring 2-selenouridine ((SeU)-U-2) and its suitably protected derivative for phosphoramidite synthesis. From known fully TBDMS-protected thiouridine, the corresponding selenouridine was synthesized via the reaction of methylthiouridine with NaHSe, which was then completely deprotected without affecting the selenocarbonyl moiety to deliver (SeU)-U-2. Next, (SeU)-U-2 was converted into the 2'-O-TBDMS-5'-O-DMT derivative in 81% yield over four steps including di-tert-butylsilylene (DTBS) introduction at O3' and O5', O2'-silylation, selective cleavage of DTBS, and DMT introduction. This synthetic route enabled gram-scale preparation of both (SeU)-U-2 and its phosphoramidite precursor in excellent yields. Furthermore, the predicted C3'-endo conformational preference of (SeU)-U-2 was experimentally confirmed by NMR spectroscopy.

  DOI：

  10.3987/com-15-13349
• 作为产物：
  描述：

  四乙酰核糖 在 咪唑 、 硫酸氢铵 、 三甲基氯硅烷 、 六甲基二硅氮烷 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 1-((2R,3R,4R,5R)-3,4-Bis((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF
  [FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS

  摘要：

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。

  公开号：

  WO2014093924A1

文献信息

• [EN] ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE ALTERNATIVES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2015196130A3

  公开（公告）日：2016-03-03
• Alternative nucleic acid molecules and uses thereof
  申请人：Moderna Therapeutics, Inc.

  公开号：EP2918275B1

  公开（公告）日：2016-05-18
• [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2014093924A1

  公开（公告）日：2014-06-19

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。
• An Efficient Synthesis of 2-Selenouridine and Its Phosphoramidite Precursor
  作者：Mamoru Koketsu、Darrell R. Davis

  DOI：10.3987/com-15-13349

  日期：——

  We describe an efficient and scalable synthetic route to the natural occurring 2-selenouridine ((SeU)-U-2) and its suitably protected derivative for phosphoramidite synthesis. From known fully TBDMS-protected thiouridine, the corresponding selenouridine was synthesized via the reaction of methylthiouridine with NaHSe, which was then completely deprotected without affecting the selenocarbonyl moiety to deliver (SeU)-U-2. Next, (SeU)-U-2 was converted into the 2'-O-TBDMS-5'-O-DMT derivative in 81% yield over four steps including di-tert-butylsilylene (DTBS) introduction at O3' and O5', O2'-silylation, selective cleavage of DTBS, and DMT introduction. This synthetic route enabled gram-scale preparation of both (SeU)-U-2 and its phosphoramidite precursor in excellent yields. Furthermore, the predicted C3'-endo conformational preference of (SeU)-U-2 was experimentally confirmed by NMR spectroscopy.