(R_P)-5'-O-dimethoxytrityl-N⁴-benzoylcytidine 3'-O-methanephosphonothioanilidate | 185685-38-5

• 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: (R_P)-5'-O-dimethoxytrityl-N⁴-benzoylcytidine 3'-O-methanephosphonothioanilidate
• 英文别名: N-[1-[(2R,4S,5R)-4-[anilino(methyl)phosphinothioyl]oxy-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 185685-38-5
• 化学式: C₄₄H₄₃N₄O₇PS
• 分子量: 802.888
• InChiKey: JIOKSYCZXJJFNF-NFTJGDBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R_P)-5'-O-dimethoxytrityl-N⁴-benzoylcytidine 3'-O-methanephosphonothioanilidate 在 Oxone 、 sodium acetate buffer 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以82%的产率得到(S_P)-5'-O-dimethoxytritylN⁴-benzoylcytidine 3'-O-methanephosphonoanilidate
  参考文献：
  名称：

  Potassium peroxymonosulfate (oxone) — An efficient oxidizing agent for phosphothio compounds

  摘要：

  Potassium peroxymonosulfate (oxone) is demonstrated as a versatile chemoselective and stereospecific oxidizing agent for phosphothio compounds. Its application in nucleotide chemistry is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00492-2
• 作为产物：
  描述：

  甲基二氯膦 、 N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 、 苯胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 作用下， 生成 (R_P)-5'-O-dimethoxytrityl-N⁴-benzoylcytidine 3'-O-methanephosphonothioanilidate 、 (S_P)-5'-O-dimethoxytrityl-N⁴-benzoylcytidine 3'-O-methanephosphonothioanilidate
  参考文献：
  名称：

  Stereochemistry of the DBU/LiCl-Assisted Nucleophilic Substitution at Phosphorus in Nucleoside-3‘-O-(Se-methyl Methanephosphonoselenolate)s

  摘要：

  The crystal and molecular structure of diastereomerically pure N-4-benzoyl-2'-deoxycytidine 3'-O-(Se-methyl methanephosphonoselenolate (FAST-eluted) (4, R = H, B = C-Bz) and 5'-O-pixylthymidine 3'-O-(S-methyl methanephosphonothiolate (FAST-eluted) (5) have been elucidated by X-ray crystallography. The absolute configuration at the phosphorus atom in both compounds is Sp. Each FAST-4' (R = DMT, B = C-Bz) and FAST-5 (R = Px, B = Thy) in the process of DBU/LiCl-assisted condensation with 3'-O-acetyl-N-4-benzoylcytidine and 3'-O-acetylthymidine gave after deprotection (S-P)-dicytidine-(3',5')-methanephosphonate and (S-P)-dithymidine-(3',5')-methanephosphonate, respectively. Unambiguous assignment of the absolute configuration at the phosphorus in 4 (R = H, B = C-Bz) and 5 (R = Pr, B = Thy) allows for stereochemical correlation and the conclusion that DBU/LiCl-assisted nucleophilic substitution at phosphorus occurs with net inversion of configuration, in contrast to our earlier erroneous deduction,(5) Moreover, the knowledge of the absolute configuration at the phosphorus atom in both 4 (R = H, B = C-Bz) and 5 (R = Px, B = Thy) allows for assignment of the absolute configuration at phosphorus in precursors of 4' and 5, such as 5'-O-DMT-nucleoside 3'-O-methanephosphonothioanilidates (6), methanephosphonoanilidates (8), and methanephosphonoselenoanilidates (9).

  DOI：

  10.1021/jo980225g

文献信息

• Stereochemistry of the DBU/LiCl-Assisted Nucleophilic Substitution at Phosphorus in Nucleoside-3‘-<i>O</i>-(<i>Se</i>-methyl Methanephosphonoselenolate)s
  作者：Lucyna A. Woźniak、Michał Wieczorek、Jarosław Pyzowski、Wiesław Majzner、Wojciech J. Stec

  DOI：10.1021/jo980225g

  日期：1998.8.1

  The crystal and molecular structure of diastereomerically pure N-4-benzoyl-2'-deoxycytidine 3'-O-(Se-methyl methanephosphonoselenolate (FAST-eluted) (4, R = H, B = C-Bz) and 5'-O-pixylthymidine 3'-O-(S-methyl methanephosphonothiolate (FAST-eluted) (5) have been elucidated by X-ray crystallography. The absolute configuration at the phosphorus atom in both compounds is Sp. Each FAST-4' (R = DMT, B = C-Bz) and FAST-5 (R = Px, B = Thy) in the process of DBU/LiCl-assisted condensation with 3'-O-acetyl-N-4-benzoylcytidine and 3'-O-acetylthymidine gave after deprotection (S-P)-dicytidine-(3',5')-methanephosphonate and (S-P)-dithymidine-(3',5')-methanephosphonate, respectively. Unambiguous assignment of the absolute configuration at the phosphorus in 4 (R = H, B = C-Bz) and 5 (R = Pr, B = Thy) allows for stereochemical correlation and the conclusion that DBU/LiCl-assisted nucleophilic substitution at phosphorus occurs with net inversion of configuration, in contrast to our earlier erroneous deduction,(5) Moreover, the knowledge of the absolute configuration at the phosphorus atom in both 4 (R = H, B = C-Bz) and 5 (R = Px, B = Thy) allows for assignment of the absolute configuration at phosphorus in precursors of 4' and 5, such as 5'-O-DMT-nucleoside 3'-O-methanephosphonothioanilidates (6), methanephosphonoanilidates (8), and methanephosphonoselenoanilidates (9).
• Potassium peroxymonosulfate (oxone) — An efficient oxidizing agent for phosphothio compounds
  作者：Lucyna A. Woźniak、Maria Koziołkiewicz、Anna Kobylańska、Wojciech J. Stec

  DOI：10.1016/s0960-894x(98)00492-2

  日期：1998.10

  Potassium peroxymonosulfate (oxone) is demonstrated as a versatile chemoselective and stereospecific oxidizing agent for phosphothio compounds. Its application in nucleotide chemistry is presented. (C) 1998 Elsevier Science Ltd. All rights reserved.