6'-carba-2'-deoxy-5'-O-tritylthymidine | 125353-62-0

• 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: 6'-carba-2'-deoxy-5'-O-tritylthymidine
• 英文别名: carbocyclic 5'-O-tritylthymidine；1-[(1R,3S,4R)-3-hydroxy-4-(trityloxymethyl)cyclopentyl]-5-methylpyrimidine-2,4-dione
• CAS: 125353-62-0
• 化学式: C₃₀H₃₀N₂O₄
• 分子量: 482.579
• InChiKey: WFGFYUXQLZXEMY-XCRWMPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6'-carba-2'-deoxy-5'-O-tritylthymidine 在 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-5-methyl-1-<4-(hydroxymethyl)-3-cyclopentenyl>-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Carbocyclic Analogues of 3′,4′-Didehydro-2′-deoxyribofuranosyl-2,4(1H,3H)-pyrimidinediones

  摘要：

  A new method for obtaining carbocyclic analogues of 3',4'-didehydro-2,4(1H,3H)-pyrimidinedione nucleosides in good yields consists of the reaction of the carbocyclic 2,3'-anhydronucleosides with lithium chloride in dimethylformamide. Small amounts of the carbocyclic 2',3'-didehydro isomers are formed simultaneously. The carbocyclic 2,3'-anhydronucleosides were obtained by treating carbocyclic 5'-trityl derivatives with DAST.

  DOI：

  10.1080/15257779408010673
• 作为产物：
  描述：

  2,1''-Anhydro-3--thymin 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 反应 314.0h， 生成 6'-carba-2'-deoxy-5'-O-tritylthymidine
  参考文献：
  名称：

  脱水胸苷的碳环类似物

  摘要：

  将胸苷的碳环类似物（C-胸苷，2）转化为3'-（O-甲磺酰基）-5'-O-三苯甲基胸苷的类似物，将其在碱性溶液中或与1,5-二氮杂双环[5.4]环合。 0]十一碳五烯（DBU）与5'-O-三苯甲基-2,3'-脱水胸苷的碳环类似物（6）。后一种化合物的水解产生了全顺式胸苷的碳环类似物。通过用DBU处理5'- O-甲磺酰基类似物，C-胸苷也被转化为3'- O-乙酰基-2,5'-脱水胸苷的碳环类似物（12）。脱水衍生物的水解得到C-胸苷。碳环类似物（3）将3'-脱氧-2'-羟基胸苷类似地转化为相应的2,2'-脱水胸苷（15）和2,5'-脱水胸苷（21）类似物。如所预期的，C-5'- O-三苯甲基-2,2'-脱水胸苷比2,3'-脱水胸苷类似物更容易形成。这些2,2'-和2,5'-脱水胸苷类似物的水解分别得到全顺式-3'-脱氧-2'-羟基胸苷和3的碳环类似物。

  DOI：

  10.1002/jhet.5570200329

文献信息

• Synthesis and Antiviral Evaluation of Carbocyclic 3′-Azidothymidine (AZT) Analogues and TheircycloSal-Phosphate Triesters
  作者：Olaf R. Ludek、Jan Balzarini、Chris Meier

  DOI：10.1002/ejoc.200500719

  日期：2006.2

  Carbocyclic analogues of the anti-HIV dideoxynucleoside 3′-azido-3′-deoxythymidine AZT (1) were synthesized. Starting from the enantiomerically pure carbocyclic 2′-deoxythymidine 2, four different carbocyclic AZT analogues 2,4–6 were prepared. Moreover, the nucleoside analogues were converted into their membrane-permeable cycloSal-phosphate triesters. All compounds were tested in vitro for their anti-HIV

  合成了抗 HIV 双脱氧核苷 3'-叠氮基-3'-脱氧胸苷 AZT (1) 的碳环类似物。从对映体纯碳环 2'-脱氧胸苷 2 开始，制备了四种不同的碳环 AZT 类似物 2,4-6。此外，核苷类似物被转化为它们的膜渗透性环磷酸三酯。所有化合物都在体外测试了它们在人 T 淋巴细胞中的抗 HIV 活性 (CEM/0)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogs derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
  作者：J. Beres、G. Sagi、I. Tomoskozi、L. Gruber、E. Baitz-Gacs、L. Otvos、E. De Clercq

  DOI：10.1021/jm00167a011

  日期：1990.5

  lesser extent, (+)-carbocyclic 2'-deoxyadenosine proved to be effective against HSV-1 [minimum inhibitory concentration (MIC): 0.2 and 2 micrograms/mL, respectively] and HSV-2 (MIC: 2 and 20 micrograms/mL, respectively), but virtually inactive against TK- HSV-1 (MIC: 40 and 100 micrograms/mL, respectively). (+)-Carbathymidine was also active against vaccinia virus (2 micrograms/mL). None of the compounds

  对映体纯的（+）-和（-）-碳环胸苷，（-）-碳环3'-表胸苷，（+）-碳环3'-脱氧-3'-叠氮胸苷，（+）-碳环2,3'从（+）-（）的常见手性库中以立体有择的方式合成了-O-脱水胸苷，（+）-碳环3'-O，6'-亚甲基胸苷和（+）-（6'S）-碳环6'-甲基胸苷（1R，5S）-和（-）-（1S，5R）-2-氧杂双环[3.3.0] oct-6-en-3-one并评估其抗病毒活性。（+）-氨基吡啶和较小程度的（+）-碳环2'-脱氧腺苷被证明对HSV-1有效[最低抑制浓度（MIC）：分别为0.2和2微克/ mL]和HSV-2 （MIC：分别为2和20微克/ mL），但实际上对TK-HSV-1没有活性（MIC：分别为40和100微克/ mL）。（+）-氨基甲酸胸苷对牛痘病毒也有活性（2微克/毫升）。这些化合物均未对HIV或其他RNA病毒的复制产生特定影响。
• A facile method for deprotection of trityl ethers using column chromatography
  作者：Ashish K Pathak、Vibha Pathak、Lainne E Seitz、Kamal N Tiwari、Mohammad S Akhtar、Robert C Reynolds

  DOI：10.1016/s0040-4039(01)01645-8

  日期：2001.10

  A mild, efficient and inexpensive detritylation method is reported that uses trifluoroacetic acid on a silica gel column to obtain pure, detritylated compounds in one-step. This method is applicable to acid stable as well as acid sensitive compounds with only slight alterations in the procedure. Nineteen examples are given. (C) 2001 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE
  作者：O. R. Ludek、C. Meier

  DOI：10.1081/ncn-200060251

  日期：2005.4.1

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.
• BERES, J.;SAGI, GY.;TOMOSKOZI, I.;GRUBER, L.;BAITZ-GACS, E.;OTVOS, L.;CLE+, J. MED. CHEM., 33,(1990) N, C. 1353-1360
  作者：BERES, J.、SAGI, GY.、TOMOSKOZI, I.、GRUBER, L.、BAITZ-GACS, E.、OTVOS, L.、CLE+

  DOI：——

  日期：——