(E)-3-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester | 156100-75-3

• 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: (E)-3-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]prop-2-enoate
• CAS: 156100-75-3
• 化学式: C₁₄H₁₇N₅O₅
• 分子量: 335.319
• InChiKey: MFGCDCJITIIKDU-IHJCATOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester 在 palladium on activated charcoal 水 、 氢气 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 3-[(2R,3S,5R)-3-{3-[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propylamino}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propionaldehyde
  参考文献：
  名称：

  The synthesis of modified achiral internucleoside linkages: -NHCH2CH2- linked oligonucleosides

  摘要：

  A method for the synthesis of oligonucleosides uniformly linked by the NHCH2CH2 moiety is described. Syntheses of heterodimers and a thymidylate trimer along with relevant T(m) and nuclease resistance data are described.

  DOI：

  10.1016/s0040-4039(00)61716-1
• 作为产物：
  描述：

  齐多夫定 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (E)-3-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acrylic acid ethyl ester
  参考文献：
  名称：

  The synthesis of modified achiral internucleoside linkages: -NHCH2CH2- linked oligonucleosides

  摘要：

  A method for the synthesis of oligonucleosides uniformly linked by the NHCH2CH2 moiety is described. Syntheses of heterodimers and a thymidylate trimer along with relevant T(m) and nuclease resistance data are described.

  DOI：

  10.1016/s0040-4039(00)61716-1

文献信息

• Synthesis and conformational studies of amide-linked cyclic homooligomers of a thymidine-based nucleoside amino acid
  作者：Tushar Kanti Chakraborty、Dipankar Koley、Sripadi Prabhakar、Rapolu Ravi、Ajit Chand Kunwar

  DOI：10.1016/j.tet.2005.07.089

  日期：2005.10

  Cyclic homooligomers of a thymidine-based nucleoside amino acid were synthesized from the linear dimer using BOP reagent in the presence of DIPEA under dilute conditions. Conformational analysis by NMR and constrained MD studies revealed that all the cyclic products had symmetrical structures. The NH and CO groups in these molecules point in opposite directions with near perpendicular orientation with

  在DIPEA的存在下，在稀释条件下，使用BOP试剂从线性二聚体合成了基于胸苷的核苷氨基酸的环状均聚物。NMR的构象分析和受约束的MD研究表明，所有环状产物均具有对称结构。这些分子中的NH和CO基团指向相对的方向，相对于在与碱相同的一侧具有CO的大环的平面，它们具有接近垂直的取向。
• BIFUNCTIONAL NUCLEOSIDES, OLIGOMERS THEREOF, AND METHODS OF MAKING AND USING THE SAME
  申请人：STERLING WINTHROP INC.

  公开号：EP0701564A1

  公开（公告）日：1996-03-20
• US5892024A
  申请人：——

  公开号：US5892024A

  公开（公告）日：1999-04-06
• [EN] BIFUNCTIONAL NUCLEOSIDES, OLIGOMERS THEREOF, AND METHODS OF MAKING AND USING THE SAME<br/>[FR] NUCLEOSIDES BIFONCTIONNELS, OLIGOMERES DESDITS NUCLEOSIDES ET PROCEDES D'OBTENTION ET D'UTILISATION DESDITS OLIGOMERES
  申请人：STERLINGWINTHROP INC.

  公开号：WO1994022888A1

  公开（公告）日：1994-10-13

  (EN) Disclosed are novel bifunctional nucleoside analogs and oligonucleosides of 3 - 4 bases (trimers and tetramers) and longer containing at least two consecutive internucleoside linkages of two carbon-one nitrogen atom or two carbon-one oxygen atom (3'-NCC-5', 3'-CNC-5', 3'-OCC-5') internucleoside linkages. The bifunctional nucleosides are useful for preparing the trimers and tetramers, which, in turn, are useful, together with the nucleosides, in preparing oligonucleosides as well as chimeric oligonucleotide analogs, preferably antisense oligonucleosides and oligonucleotide analogs, of 6 to about 60 bases having at least two consecutive internucleoside linkages of two carbon atoms and one nitrogen atom or 2 carbon atoms and one oxygen atom in the oligonucleoside backbone.(FR) On décrit de nouveaux analogues de nucléosides bifonctionnels et des oligonucléosides à 3 ou 4 bases (trimères et tétramères) ou plus longs, contenant au moins deux liaisons internucléosides consécutives. Ces liaisons sont formées par deux atomes de carbone et un atome d'azote, ou deux atomes de carbone et un atome d'oxygène (3'NCC-5', 3'CNC-5', 3'-OCC-5'). Lesdits nucléosides bifonctionnels sont utiles pour la préparation de trimères et de tétramères qui, à leur tour, sont utiles avec les nucléosides, pour la préparation d'oligonucléosides, aussi bien que d'analogues d'oligonucléotides chimériques, de préférence des oligonucléosides et des analogues d'oligonucléotides antisens, comportant de 6 à environ 60 bases possédant au moins deux liaisons internucléosides consécutives constituées par deux atomes carbone et un atome d'azote ou par deux atomes de carbone et un atome d'oxygène dans le squelette de l'oligonucléoside.
• The synthesis of modified achiral internucleoside linkages: -NHCH2CH2- linked oligonucleosides
  作者：Ashis K. Saha、Wayne Schairer、Cheryl Waychunas、C.V.C. Prasad、Mark Sardaro、Donald A. Upso、Lawrence I. Kruse

  DOI：10.1016/s0040-4039(00)61716-1

  日期：1993.9

  A method for the synthesis of oligonucleosides uniformly linked by the NHCH2CH2 moiety is described. Syntheses of heterodimers and a thymidylate trimer along with relevant T(m) and nuclease resistance data are described.