5'-O-benzylthymidine | 124314-25-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-benzylthymidine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(phenylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 124314-25-6
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: OGURBCHBHNRDJK-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-O-benzylthymidine 生成 beta-胸苷
  参考文献：
  名称：

  OKAUCHI, TATSUO;KUBOTA, HIDEKI;NARASAKA, KOICHI, CHEM. LETT.,(1989) N, C. 801-804

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phenylmethoxymethyl)oxolan-3-yl] 2-acetamidoacetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以95%的产率得到5'-O-benzylthymidine
  参考文献：
  名称：

  Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group

  摘要：

  A facile synthesis of 2'-deoxy-beta-ribonucleosides from 3'-O-(N-acetyl)-glycyl-protected 2'-deoxyribofuranose has been developed. The coupling reactions between the protected 2'-deoxyribose and silylated bases exhibited beta-selectivity up to 98% presumably via a 1',3'-participation mechanism. The 3'-directing group can be introduced and removed easily under mild conditions. This approach provides an efficient and highly stereoselective entry for the synthesis of 2'-deoxy-ribonucleosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.006

文献信息

• Catalytic Stereoselective Synthesis of Pyrimidine 2-Deoxyribonucleosides
  作者：Teruaki Mukaiyama、Noriyuki Hirano、Minoru Nishida、Hiromi Uchiro

  DOI：10.1246/cl.1996.99

  日期：1996.2

  Highly stereoselective synthesis of β-d-deoxyribonucleosides from 1-O-acetyl-5-O-benzyl-2-deoxy-3-diethylthiocarbamoyl ribofuranoside (3) is performed by the reaction with silylated pyrimidine nucleobases in the presence of a catalytic amount of several Lewis acids.

  在催化量的几种路易斯酸存在下，通过与硅化的嘧啶核苷碱基反应，对1-O-乙酰基-5-O-苄基-2-脱氧-3-二乙基硫代氨基甲酰呋喃核糖苷（3）进行高度立体选择性合成。
• ANTISENSE NUCLEIC ACID DERIVATIVE
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0558749A1

  公开（公告）日：1993-09-08

  A compound represented by general formula (1), its salt, and antiviral and antitumor drugs containing the same, wherein k is 0 to 20; m is 0 or 1; n is 4 to 29; X represents OH, methyl, sulfhydryl, C₁ to C₄ alkoxy or C₁ to C₆ monoalkylamino; Y and Z represent each O or S; R¹, R² and R³ may be the same or different from each other and each represents H, C₁ to C₆ alkyl, or C₆ to C₁₀ aryl which may have the substitutent(s) of group α; and D and B represent each independently a residue of any of the compounds of group β; provided that m is 0 when k is 0, and a base sequence containing B is complementary to a tumor gene or a virus gene: group α: OH, C₁ to C₆ alkyl, C₁ to C₆ alkoxy, methylenedioxy, nitro, azido, halogen, C₆ to C₁₀ aryl, C₆ to C₁₀ aryloxy, and aralkyloxy composed of a C₆ to C₁₀ aryl moiety and a C₁ to C₂ alkyl moiety, group β: adenine guanine, cytosine and thymine.

  通式(1)代表的化合物、其盐以及含有该通式的抗病毒和抗肿瘤药物，其中 k 为 0 至 20；m 为 0 或 1；n 为 4 至 29；X 代表 OH、甲基、巯基、C₁ 至 C₄ 烷氧基或 C₁ 至 C₆ 单烷基氨基；Y 和 Z 各自代表 O 或 S；R¹、R²和R³可以相同或不同，各自代表H、C₁至C₆烷基或C₆至C₁₀芳基，可具有α基团的取代基；D和B各自独立地代表β基团的任何化合物的残基；条件是当k为0时，m为0，且含有B的碱基序列与肿瘤基因或病毒基因互补：第 α 组OH, C₁ to C₆ alkyl, C₁ to C₆ alkoxy, methylenedioxy, nitro, azido, halogen, C₆ to C₁₀ aryl, C₆ to C₁₀ aryloxy, and aralkyloxy composed of a C₆ to C₁₀ aryl moiety and a C₁ to C₂ alkyl moiety, group β：腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶。
• Biologically Active Oligodeoxyribonucleotides - II¹: Structure Activity Relationships of Anti-HIV-1 Pentadecadeoxyribonucleotides Bearing 5′-End-Modifications
  作者：Hitoshi Hotoda、Kenji Momota、Hidehiko Furukawa、Takemichi Nakamura、Masakatsu Kaneko、Satcshi Kimura、Kawu Shimada

  DOI：10.1080/15257779408012159

  日期：1994.7

  5'-End-modified pentadecadeoxyribonucleotides (15mers) with a sequence complementary to the tat 2nd splicing acceptor region of human immunodeficiency virus type 1 (HIV-1) were prepared and evaluated for anti-HIV-1 activity. The structures of modified 15mers were confirmed by negative ion LSI mass spectroscopy, and the anti-HIV-1 activities were evaluated in vitro by MTT assay using MT-4 cells. While the unmodified 15mer had no activity in our assay system, the 15mers bearing modifications with trityl-type substituents at the 5'-end showed potent anti-HIV-1 activities.
• The effect of the base in the fragmentation of nucleotide C4′ radicals
  作者：David Crich、Dae-Hwan Suk、Xiaolin Hao

  DOI：10.1016/s0040-4020(02)00557-4

  日期：2002.7

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• OKAUCHI, TATSUO;KUBOTA, HIDEKI;NARASAKA, KOICHI, CHEM. LETT.,(1989) N, C. 801-804
  作者：OKAUCHI, TATSUO、KUBOTA, HIDEKI、NARASAKA, KOICHI

  DOI：——

  日期：——