(1R)-1,4-脱水-2-脱氧-1-(1,3-二甲基-2,4-二氧代-1,2,3,4-四氢-5-嘧啶基)-D-赤式-戊糖醇 | 65358-16-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: (1R)-1,4-脱水-2-脱氧-1-(1,3-二甲基-2,4-二氧代-1,2,3,4-四氢-5-嘧啶基)-D-赤式-戊糖醇
• 英文名称: 1,3-Dimethyl-2'-deoxypseudouridine
• 英文别名: 5-(2'-deoxy-β-D-threo-pentofuranosyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；1,3-dimethyl-2'-deoxy-ψ-uridine；2'-Deoxy-1,3-dimethyl-ψ-uridine；2'-deoxy-1,3-dimethylpseudouridine；5-(β-D-erythro-2-deoxy-pentofuranosyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione；1,3-dimethyl-2'-deoxy-pseudouridine；5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 65358-16-9
• 化学式: C₁₁H₁₆N₂O₅
• 分子量: 256.258
• InChiKey: VUFZJLBBVTWRKA-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1,4-脱水-2-脱氧-1-(1,3-二甲基-2,4-二氧代-1,2,3,4-四氢-5-嘧啶基)-D-赤式-戊糖醇 在 盐酸胍 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 以16%的产率得到2-氨基-5-(2-脱氧-beta-D-赤式-呋喃戊糖基)-4(1H)-嘧啶酮
  参考文献：
  名称：

  Nucleosides. 120. Syntheses of 2'-deoxy-.psi.-isocytidine and 2'-deoxy-1-methyl-.psi.-uridine from .psi.-uridine

  摘要：

  DOI：

  10.1021/jo00331a005
• 作为产物：
  描述：

  假尿苷 在 偶氮二异丁腈 、 三正丁基氢锡 、 2-乙酰氧基异丁酰氯 作用下， 反应 51.5h， 生成 (1R)-1,4-脱水-2-脱氧-1-(1,3-二甲基-2,4-二氧代-1,2,3,4-四氢-5-嘧啶基)-D-赤式-戊糖醇
  参考文献：
  名称：

  Nucleosides. 120. Syntheses of 2'-deoxy-.psi.-isocytidine and 2'-deoxy-1-methyl-.psi.-uridine from .psi.-uridine

  摘要：

  DOI：

  10.1021/jo00331a005

文献信息

• Nucleosides.<b>130</b>. Synthesis of 2′-Deoxy-2′-substituted- and 5′-Deoxy-5′-substituted-ψ-uridine Derivatives. Crystalline and Molecular Structure of 2′-Chloro-2′-deoxy-1,3-dimethyl-ψ-uridine. Studies Directed Toward the Synthesis of 2′-Deoxy-2′-substituted-<i>arabino</i>-Nucleosides.<b>1</b>
  作者：Krzysztof W. Pankiewicz、Kyoichi A. Watanabe、Hiroaki Takayanagi、Tsueno Itoh、Haruo Ogura

  DOI：10.1002/jhet.5570220646

  日期：1985.11

  5′-deoxy-5′-substituted-ψ-uridine derivatives 4 from 3′,5′-O-(1, 1, 3, 3-tetraisopropyldisiloxanyl)-1,3-dimethyl-ψ-uridine 1 via a silyl rearrangement reaction. Nucleophilic displacement of the mesyloxy function of 2′-O-mesyl-1,3-dimethyl-ψ-uridine 7 afforded products with the 2′-substituent in the “down” ribo configuration 8. X-Ray crystallographic analysis of the 2′-chloro derivative 8a firmly established the

  开发了一种从3'，5'- O-（1，1，3，3-四异丙基二硅氧烷基）-1,3-二甲基-ψ-制备5'-脱氧-5'-取代-ψ-尿苷衍生物4的方法尿苷1通过甲硅烷基重排反应。2' - O-甲磺酰基-1,3-二甲基-ψ-尿苷7的甲磺酰氧基功能的亲核取代提供了带有2'-取代基的“向下”核糖构型的产品8。2'-氯衍生物8a的X射线晶体学分析牢固地建立了8的分子结构，并为相邻基团参与7的4-羰基官能团提供了证据。 在亲核反应中。
• Nucleosides. 121. Improved and general synthesis of 2'-deoxy-C-nucleosides. Synthesis of 5-(2-deoxy-.beta.-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine
  作者：Krzysztof Pankiewicz、Akira Matsuda、Kyoichi A. Watanabe

  DOI：10.1021/jo00342a022

  日期：1982.1
• Chu,C.K. et al., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 1119 - 1121
  作者：Chu,C.K. et al.

  DOI：——

  日期：——
• A Facile Synthesis of the Phosphoramidites of 2-<i>N</i>-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1, 3-Dimethyl-2′-deoxy-ψ-uridine and<i>N</i>1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis
  作者：B. K. Bhattacharya、G. R. Revankar

  DOI：10.1080/15257779408009476

  日期：1994.9

  An efficient and facile syntheses of 5'-O-(4,4'-dimethoxytrityl)-3'-[2-cyanoethyl bis(1-methylethyl)]phosphoramidites of 2-N-methyl-2'-deoxy-psi-isocytidine (h), 2-N-methyl-2'-deoxy-alpha-psi-isocytidine (13 ), 2-N-methyl-2'-O-allyl-psi-isocytidine (11), 1,3-dimethyl-2'-deoxy-psi-uridine (4) and N1-methyl-2'-O-allyl-psi-uridine (19) have been accomplished in good overall yields. The pyrimidine-pyrimidine transformation reaction was found to be useful for the preparation of 2-N-methyl-2'-O-allyl-psi-isocytidine (10). The utility of these novel phosphoramidites is demonstrated by their incorporation into oligonucleotides via solid-support, oligonucleotide methodology.
• Facile synthesis of 2'-deoxy-3'-keto- and 2'-deoxypseudouridine derivatives and analogues. Palladium(II)-mediated coupling reactions of furanoid glycals
  作者：Jane Chi Ya Cheng、Uli Hacksell、G. Doyle Daves

  DOI：10.1021/jo00366a003

  日期：1986.8