Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-acetylamino-purin-9-yl)-5-(4-oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester | 890533-26-3

• 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: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-acetylamino-purin-9-yl)-5-(4-oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4R,5R)-5-(6-acetamidopurin-9-yl)-4-acetyloxy-2-[(4-oxo-1,3,2-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-3-yl] acetate
• CAS: 890533-26-3
• 化学式: C₂₃H₂₂N₅O₁₀P
• 分子量: 559.429
• InChiKey: BSLREKGTSSDRJQ-GWLNLEPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-acetylamino-purin-9-yl)-5-(4-oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester 在 吡啶 、 三正丁胺 、 碘 、 三丁基焦磷酸铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 N-[9-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[(4-hydroxy-2,6-dioxido-4,6-dioxo-1,3,5,2,4lambda5,6lambda5-trioxatriphosphinan-2-ium-2-yl)oxymethyl]oxolan-2-yl]purin-6-yl]ethanimidate
  参考文献：
  名称：

  One-Flask Synthesis of Dinucleoside Tetra- and Pentaphosphates

  摘要：

  We report a one-flask route for the synthesis of dinucleoside tetra- and pentaphosphates, in isolated yields of 50-85%. This route relies on a mixture of P(Ill) and P(V) chemistries, using phosphitylation of a protected nucleoside with 2-chloro-4H-1,3,2-benzo-dioxaphosphorin-4-one (salicylchlorophosphite), followed by sequential reaction with inorganic pyrophosphate and a nucleoside 5' mono- or diphosphate.

  DOI：

  10.1021/ol060491d
• 作为产物：
  描述：

  6-acetylamino-9-[(2,3-di-O-acetyl)-β-D-ribofuranosyl]purine 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(6-acetylamino-purin-9-yl)-5-(4-oxo-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  One-Flask Synthesis of Dinucleoside Tetra- and Pentaphosphates

  摘要：

  We report a one-flask route for the synthesis of dinucleoside tetra- and pentaphosphates, in isolated yields of 50-85%. This route relies on a mixture of P(Ill) and P(V) chemistries, using phosphitylation of a protected nucleoside with 2-chloro-4H-1,3,2-benzo-dioxaphosphorin-4-one (salicylchlorophosphite), followed by sequential reaction with inorganic pyrophosphate and a nucleoside 5' mono- or diphosphate.

  DOI：

  10.1021/ol060491d

文献信息

• Synthesis of boranoate, selenoate, and thioate analogs of AZTp4A and Ap4A
  作者：Qianwei Han、Stefan G. Sarafianos、Eddy Arnold、Michael A. Parniak、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1016/j.tet.2009.07.079

  日期：2009.9

  We report efficient, one-flask procedures for the synthesis of a family of 14 analogs of AZTp(4)A and Ap(4)A containing BH3, S, or Se, along with two bisphosphonate analogs of Ap(4)A. These compounds should slow unwanted enzymatic hydrolysis and have the potential to create unique binding interactions in biochemical and structural Studies of the excision reaction responsible for resistance of HIV-1 to AZT, as well as assist in drug design. (C) 2009 Elsevier Ltd. All rights reserved.