benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-hydroxytetrahydrothien-3-yl ester | 917377-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-hydroxytetrahydrothien-3-yl ester
• CAS: 917377-28-7
• 化学式: C₂₈H₃₂O₄SSi
• 分子量: 492.711
• InChiKey: XDCFKJFEGKTWKJ-CYXNTTPDSA-N

物化性质

• 沸点：
  576.0±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-hydroxytetrahydrothien-3-yl ester 在 二乙胺基三氟化硫 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (-)-1-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066
• 作为产物：
  描述：

  (3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 生成 benzoic acid (-)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-hydroxytetrahydrothien-3-yl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066

文献信息

• SYNTHESIS AND ANTIVIRAL ACTIVITY OF<scp>D</scp>- AND<scp>L</scp>-2′-AZIDO-2′,3′-DIDEOXY-4′-THIOPYRIMIDINE AND PURINE NUCLEOSIDES
  作者：Lak Shin Jeong、Yun Ha Kim、Hea Ok Kim、Su Jeong Yoo、Yong Hee Park、Sook Hee Yeon、Moon Woo Chun、Hee-Doo Kim

  DOI：10.1081/ncn-100002346

  日期：2001.3.31

  Novel D- and L-2'-azido-2',3'-dideoxy-4'-thionucleosides were synthesized starting from L- and D-xylose via D- and L-4-thioarabitol derivative as key intermediates and evaluated for antiviral activity, respectively. When the final nucleosides were tested against HIV-1, HSV-1, HSV-2, and HCMV, they were found to be only active against HCMV without cytotoxicity up to 100 micrograms/ml.

  从L-和D-木糖开始，以D-和L-4-硫代阿拉伯糖醇衍生物为关键中间体，合成了新的D-和L-2'-叠氮基-2'，3'-二脱氧-4'-硫代核苷，并评估了其抗病毒活性活动。当对最终核苷进行针对HIV-1，HSV-1，HSV-2和HCMV的测试时，发现它们仅对HCMV具有活性，而对细胞的毒性却高达100微克/毫升。
• Design, Enantiopure Synthesis, and Biological Evaluation of Novel ISO-D-2′,3′-Dideoxy-3′-Fluorothianucleoside Derivatives as a bioisostere of Lamivudine
  作者：Kyung Ran Kim、Ah-Young Park、Hyung Ryong Moon、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1080/15257770701506426

  日期：2007.11.26

  Novel isoD-2',3'-dideoxythianucleoside derivatives 1-3 were designed and asymmetrically synthesized to search for new anti-HIV agents. Final compounds 1-3 were evaluated against a variety of viruses including HIV-1 and 2. Only cytosine analog 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso 2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent.