3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one | 212776-53-9

• 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: 3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one
• CAS: 212776-53-9
• 化学式: C₂₁H₂₄O₃Si
• 分子量: 352.505
• InChiKey: ZMZIXQSOOKICQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one 在 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Apio Dideoxy Nucleosides with Azido or Amino Substituent

  摘要：

  Novel apio dideoxynucleosides with azido or amino substituent synthesized starting from 1,3-dihydroxyacetone utilizing an acid-catalyzed 1,4-conjugated addition as a key step and evaluated for antiviral activity. Unfortunately, they were found to be neither active against HIV-1, HSV-1,2 and poliovirus nor toxic.

  DOI：

  10.1080/07328319808003481
• 作为产物：
  描述：

  4-(tert-butyldimethylsilanyloxy)-3-(tert-butyldimethylsilanyloxymethyl)but-2-enoic acid ethyl ester 在 咪唑 、 硫酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Apio Dideoxy Nucleosides with Azido or Amino Substituent

  摘要：

  Novel apio dideoxynucleosides with azido or amino substituent synthesized starting from 1,3-dihydroxyacetone utilizing an acid-catalyzed 1,4-conjugated addition as a key step and evaluated for antiviral activity. Unfortunately, they were found to be neither active against HIV-1, HSV-1,2 and poliovirus nor toxic.

  DOI：

  10.1080/07328319808003481

文献信息

• Syntheses and Structure−Activity Relationships of Novel Apio and Thioapio Dideoxydidehydronucleosides as Anti-HCMV Agents
  作者：Lak Shin Jeong、Hea Ok Kim、Hyung Ryong Moon、Joon Hee Hong、Su Jeong Yoo、Won Jun Choi、Moon Woo Chun、Chong-Kyo Lee

  DOI：10.1021/jm000342f

  日期：2001.3.1

  acid produced from the basic hydrolysis of thioacetate 16. The majority of apio analogues synthesized in this study exhibited moderate to potent anti-HCMV activity, among which the 5-fluorouracil derivative 13c was found to be the most potent against HCMV, while thioapio analogues showed no activity against HCMV. However, all synthesized compounds did not exhibit any significant activities against HIV-1

  基于其中呋喃糖氧和2,3-二脱氧核糖的C2发生转位的apio双脱氧核苷，显示出有效的抗HIV活性和2'，3'-dideoxy-2'，3'-didehydronucleosides还显示出有效的抗HIV活性，我们合成了apio双脱氧二氢核苷，其中的氧原子与2,3-dideoxy-2,3-didehydro核糖的双键交换了。由于硫起氧的生物等排体的作用，因此也合成了硫代双脱氧二氢核苷。以苯基硒烯基化学为关键步骤，从1,3-二羟基丙酮开始合成Apio二脱氧二氢核苷13a-f。在路易斯酸存在下，在核苷碱基与乙酸苯硒烯基酯11缩合期间，异头物混合物的比例可在1：1至5：1之间变化。这与其他糖基供体例如5-O-（叔丁基二苯基甲硅烷基）-2-苯基硒烯基-2,3-二脱氧核糖基乙酸酯相反，其显示出优异的邻近基团效应（α：β= 1:99）。由内酯9经由硫代内酯17作为主要中间体合成了内酯9的硫代二脱氧二氢核苷
• Total synthesis of (±)-iso-d4T as potential antiviral agent
  作者：Lak Shin Jeong、Young A Lee、Hyung Ryong Moon、Su Jeong Yoo、Su Youn Kim

  DOI：10.1016/s0040-4039(98)01634-7

  日期：1998.10

  (+/-)-Iso-d4T which may act as a bioisostere of d4T was synthesized from 1,3-dihydroxyacetone using phenyl selenenium chemistry as a key step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  (+/−)-Iso-d4T 可能作为 d4T 的生物同系物，由 1,3-二羟基丙酮合成，其中苯基硒化学是关键步骤。© 1998 Elsevier Science Ltd. 版权所有。
• STRUCTURE-ACTIVITY RELATIONSHIPS OF APIO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
  作者：Lak Shin Jeong、Hyung Ryong Moon、Jun Hee Hong、Su Jeong Yoo、Won Jun Choi、Hea Ok Kim、Hee Sung Ahn、Hye Woo Baek、Moon Woo Chun、Hee-Doo Kim、Jeongmin Kim、Jong-Ryoo Choi

  DOI：10.1081/ncn-100002344

  日期：2001.3.31

  Several types of novel apio nucleosides were synthesized starting from 1,3-dihydroxyacetone and evaluated for antiviral activity. Among compounds tested, amino substituted apio dideoxynucleosides exhibited anti-HBV activity, while thioapio dideoxynucleosides were found to be active against HIV-1. Apio dideoxydidehydro nucleosides showed moderate to potent anti-HCMV activity, but their bioisosteric thioapio dideoxydidehydro nucleosides did not exhibit any significant antiviral activity.