[1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] [(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl carbonate | 200264-32-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] [(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl carbonate
• CAS: 200264-32-0
• 化学式: C₃₅H₃₃N₅O₁₁
• 分子量: 699.674
• InChiKey: BPYLQUFCMQQAMB-OJCHJFQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] [(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl carbonate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到[(2R,3S,5R)-3-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] carbonate
  参考文献：
  名称：

  Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites

  摘要：

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.

  DOI：

  10.1021/jo970872s
• 作为产物：
  描述：

  (3',5'-dimethoxyphenyl)phenylethane-1,2-dione 在 吡啶 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 生成 [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] [(2R,3S,5R)-3-hydroxy-5-[6-oxo-2-[(2-phenoxyacetyl)amino]-1H-purin-9-yl]oxolan-2-yl]methyl carbonate
  参考文献：
  名称：

  Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites

  摘要：

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.

  DOI：

  10.1021/jo970872s

文献信息

• Proofing of Photolithographic DNA Synthesis with 3‘,5‘-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites
  作者：Michael C. Pirrung、Lara Fallon、Glenn McGall

  DOI：10.1021/jo970872s

  日期：1998.1.1

  We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5'-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 x 4 array of 16 decanucleotides of the sequence 5'-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5'-CTGAACG-GTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.