2-C,2-O-didehydro-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose | 229469-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-C,2-O-didehydro-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose
• 英文别名: 2-C,2-O-didehydro-1(α)-O-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose；(6aR,8S,9aR)-8-methoxy-2,2,4,4-tetra(propan-2-yl)-6a,9a-dihydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-one
• CAS: 229469-28-7
• 化学式: C₁₈H₃₆O₆Si₂
• 分子量: 404.651
• InChiKey: WREJRRJEEAUHNM-NXHRZFHOSA-N

物化性质

• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-C,2-O-didehydro-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose 在 吡啶 、 sodium perborate 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 sodium tert-pentoxide 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 二甲基亚砜 、 苯 为溶剂， 反应 39.5h， 生成 (2S,3S,4R,5S)-4-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-methoxy-3-phenylmethoxyoxolane-2-carbaldehyde
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 在 吡啶 、 草酸 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 反应 8.5h， 生成 2-C,2-O-didehydro-1-α-methyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-D-ribofuranose
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4

文献信息

• Synthesis and Cytotoxicity of 4-Amino-5-oxopyrido[2,3-<i>d</i>]pyrimidine Nucleosides
  作者：Jean-Luc Girardet、Esmir Gunic、Cathey Esler、Dariusz Cieslak、Zbigniew Pietrzkowski、Guangyi Wang

  DOI：10.1021/jm000073t

  日期：2000.10.1

  1-O-acetylated pentose sugar derivatives were condensed with silylated 4-amino-5-oxopyrido[2,3-d]pyrimidine, followed by protection, to afford a series of 4-amino-5-oxopyrido[2, 3-d]pyrimidine nucleosides. Further derivatizations provided an additional group of pyrido[2,3-d]pyrimidine nucleosides. These nucleosides were evaluated for in vitro cytotoxicity to human prostate cancer (HTB-81) and mouse melanoma

  许多核苷类似物已被临床用作抗癌药物或已在临床研究中进行了评估，而新的核苷类似物继续显示出希望。在本文中，我们报告了一系列新的吡啶并[2,3-d]嘧啶核苷的合成和细胞毒性。通过两个步骤将2-氨基-3-氰基-4-甲氧基吡啶转化为4-氨基-5-氧代吡啶并[2,3-d]嘧啶。将各种1-O-乙酰化戊糖衍生物与甲硅烷基化的4-氨基-5-氧代吡啶并[2,3-d]嘧啶缩合，然后进行保护，得到一系列的4-氨基-5-氧代吡啶并[2， 3-d]嘧啶核苷。进一步的衍生化提供了另外的吡啶基[2，3-d]嘧啶核苷基团。评估了这些核苷对人前列腺癌（HTB-81）和小鼠黑素瘤（B16）细胞以及正常人成纤维细胞（NHF）的体外细胞毒性。许多化合物（1a，b，2a-c，f，3f + 4d）对癌细胞具有明显的细胞毒性，其中4-氨基-5-氧代-8-（β-D-呋喃呋喃糖基）吡啶并[2,3- d]嘧啶（1b）是所有类型细胞中最有效的增殖抑制剂（EC（50）：0
• [EN] SUBSTITUTED NUCLEOSIDE AND NUCLEOTIDE ANALOGS<br/>[FR] NUCLEOSIDE SUBSTITUE ET ANALOGUES NUCLEOTIDIQUES
  申请人：ALIOS BIOPHARMA INC

  公开号：WO2010108140A1

  公开（公告）日：2010-09-23

  Disclosed herein are nucleotide analogs with protected phosphates, methods of synthesizing nucleotide analogs with protected phosphates and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the nucleotide analogs with protected phosphates.

  本文披露了具有保护磷酸酯基团的核苷酸类似物，以及合成具有保护磷酸酯基团的核苷酸类似物的方法，以及利用具有保护磷酸酯基团的核苷酸类似物治疗病毒感染、癌症和/或寄生虫病等疾病和/或症状的方法。
• Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides
  作者：Guangyi Wang、Jean-Luc Girardet、Esmir Gunic

  DOI：10.1016/s0040-4020(99)00394-4

  日期：1999.6

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.