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2-[[(2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylsulfanyl]acetic acid | 945420-87-1

中文名称
——
中文别名
——
英文名称
2-[[(2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylsulfanyl]acetic acid
英文别名
——
2-[[(2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylsulfanyl]acetic acid化学式
CAS
945420-87-1
化学式
C18H30N2O6SSi
mdl
——
分子量
430.597
InChiKey
UXJVZTLUHSMBHG-BFHYXJOUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.34
  • 重原子数:
    28
  • 可旋转键数:
    8
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.72
  • 拓扑面积:
    131
  • 氢给体数:
    2
  • 氢受体数:
    7

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-[[(2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methylsulfanyl]acetic acid四氮唑四丁基氟化铵1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下, 以 四氢呋喃二氯甲烷乙腈 为溶剂, 反应 14.0h, 生成
    参考文献:
    名称:
    Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures
    摘要:
    Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.
    DOI:
    10.1021/ol070990u
  • 作为产物:
    参考文献:
    名称:
    Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures
    摘要:
    Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.
    DOI:
    10.1021/ol070990u
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文献信息

  • Probing Binding Preferences of DNA and RNA: Backbone Chirality of Thioacetamido-Linked Nucleic Acids and <i>iso-</i>Thioacetamido-Linked Nucleic Acids to Differentiate DNA versus RNA Selective Binding
    作者:Sachin S. Gokhale、Khirud Gogoi、Vaijayanti A. Kumar
    DOI:10.1021/jo1014036
    日期:2010.11.5
    spectral differences for the dimer blocks were found to be identical for those found in phosphodiester linked ribo/xylo dimers, the 5-atom thioactamido linker could reverse the RNA binding selectivity to DNA binding selectivity by the change in configuration at the 3′-amino-substituted sugar.
    RNA和DNA双链体几何结构的细微差异可以通过硫代乙酰氨基连接的核酸和异硫代乙酰氨基连接的核酸修饰的低聚物的5原子硫代乙酰氨基连接子中3'-氨基官能团的立体化学变化来感知。与3'-核糖或木糖基氨基核苷的优选N型糖构象相反,在二聚体中发现了主要的S型糖构象。尽管发现二聚体嵌段的CD光谱差异与磷酸二酯连接的核糖/木二聚体中的CD光谱差异相同,但5原子硫代乙酰氨基接头可通过3'端构型的改变将RNA结合选择性逆转为DNA结合选择性。 -氨基取代的糖。
  • Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures
    作者:Khirud Gogoi、Anita D. Gunjal、Usha D. Phalgune、Vaijayanti A. Kumar
    DOI:10.1021/ol070990u
    日期:2007.7.1
    Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.
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同类化合物

鲁西他滨 化合物 T14195 [1,1'-联苯基]-2,3,3',4,4',5'-六醇 [(2R,3R,5S)-3-(氨基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]N-[[(2R,3S,5R)-3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基]氨基甲酸酯 9-(2-S-苯甲基-5-脱氧-2-硫代五呋喃糖基)-9H-嘌呤-6-胺 5-脱氧胸苷 5-脱氧-5-[(碘乙酰基)氨基]-胸腺嘧啶脱氧核苷 5-碘-5-脱氧胸腺嘧啶脱氧核苷 5-氨基-5-脱氧胸腺嘧啶脱氧核苷 5-氨基-2,5-二脱氧腺苷酸 5-叠氮基-5-脱氧胸腺嘧啶脱氧核苷 5-三氟乙酰氨基-5-脱氧胸腺嘧啶脱氧核苷 5'-脱氧-5'氟胸苷 5'-脱氧-5'-{[4-(甲硫基)苯胺基羰基]氨基}胸苷 5'-脱氧-5'-{[3-(甲硫基)苯胺基羰基]氨基}胸苷 5'-脱氧-5'-[4-苯基-(1,2,3)三唑-1-基]胸苷 5'-脱氧-5'-[4-(吡啶-3-基)-(1,2,3)三唑-1-基]胸苷 5'-脱氧-5'-[4-(4-氟苯基)-(1,2,3)三唑-1-基]胸苷 5'-硫代-胸苷3',5'-二乙酸酯 5'-溴乙酰氨基-5'-脱氧胸苷 5'-氨基-5-碘-2',5'-二脱氧尿苷 2-氯-N-[[3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基]乙酰胺 2,5-二脱氧腺苷 2',5'-二脱氧尿苷 1-[(2R,4S,5R)-4-羟基-5-(异氰基甲基)四氢呋喃-2-基]嘧啶-2,4-二酮 1-[(2R,4S,5R)-4-羟基-5-(异氰基甲基)四氢呋喃-2-基]-5-甲基嘧啶-2,4-二酮 1-(2,5-二脱氧-2-氟-β-D-呋喃阿拉伯糖基)嘧啶-2,4(1H,3H)-二酮 1-(2,5-二脱氧-2-氟-β-D-呋喃阿拉伯糖基)-5-碘嘧啶-2,4(1H,3H)-二酮 1-citosin-1-yl-1,2,5-trideoxy-α-L-threo-pentofuranos-4-yloxymethylphosphonic acid 9-[2,5-dideoxy-2-fluoro-5-[N-(N-2-hydroxybenzoyl)sulfamoyl]amino-β-D-ribofuranosyl]adenine triethylammonium salt 5'-amino-2',5'-dideoxy-2'-fuorouridine 1-(5'-deoxythymidin-5'-yl)-4-[methyloxycarbonyl-(2'-deoxy-2',2'-difluorocytidin-4N-yl)]-1H-1,2,3-triazole 2',5'-dideoxy-2'-(3,5-dimethoxybenzamido)-5'-(cyclohexylacetamido)adenosine 2',5'-dideoxy-2'-(3'',5''-dimethoxybenzamido)-5'-(diphenylacetamido)adenosine 2',5'-dideoxy-5'-(hydroxyethylthio)adenosine 1-(5-azido-2,5-dideoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethyluracil 1-(5'-deoxythymidin-5'-yl)-4-[methyl-(2'-deoxy-2',2'-difluorocytidin-4N-yl)]-1H-1,2,3-triazole 4′-C-azidomethyl-2′-deoxy-2′-fluorouridine 2',5'-dideoxy-6-thioguanosine thymidylyl (3'-5') 5'-seleno-5'-deoxythymidine 3'-O-(t-butyldimethylsilyl)-4'-α-methylthymidine (E)- and (Z)-5-(2-bromovinyl)-1-(5-chloro-2,5-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one N-<1,2,5-trideoxy-1β-(5-fluoro-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)-D-ribofuranos-5-yl>succinamic acid N-butyl-N'-<1,2,5-trideoxy-1β-(5-fluoro-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)-D-ribofuranose-5-yl>maleamide N-<1,2,5-trideoxy-1β-(5-fluoro-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)-D-ribofuranos-5-yl>maleamic acid 4'-chloromethyl-2'-deoxy-2',2'-difluorocytidine 4'-chloromethyl-2'-deoxy-2'-fluoro-3'-O-(L-valinyl)cytidine dihydrochloride 5'-deoxy-5'-{4-[2-(3-oxo-3H-benzo[f]chromen-1-yl)acetamidomethyl]-1H-1,2,3-triazol-1-yl}thymidine N6-benzoyl-3'-O-t-butyldimethylsilyl-5'-sulfamoylazido-2',5'-dideoxyadenosine N-{9-[(2R,4S,5R)-5-(Acetylamino-methyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide