(1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol | 952418-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol
• 英文别名: (+)-(R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-1-(tert-butyldiphenylsilyloxymethyl)-2-propen-1-ol；(2R)-1-[tert-butyl(diphenyl)silyl]oxy-2-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-2-ol
• CAS: 952418-10-9
• 化学式: C₂₇H₃₆O₄Si
• 分子量: 452.666
• InChiKey: MRMXJVYBAQQFMN-NLJOTIRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol 在 吡啶 、 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氨 、 碘 、 三溴化硼 、 N-氟代双苯磺酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 74.75h， 生成 O-((8S,9S,9aR)-8-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-7-fluoro-2,2,4,4-tetraisopropyl-6,8,9,9a-tetrahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl) O-phenyl carbonothioate
  参考文献：
  名称：

  Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity

  摘要：

  On the basis of the potent biological activity of cyclopentenyl-pyrimidines, fluorocyclopentenyl-pyrimidines were designed and synthesized from D-ribose. Among these, the cytosine derivative 5a showed highly potent antigrowth effects in a broad range of tumor cell lines and very potent antitumor activity in a nude mouse tumor xenograft model implanted with A549 human lung cancer cells. However, its 2'-deoxycytidine derivative 5b did not show any antigrowth effects, indicating that 2'-hydroxyl group is essential for the biological activity.

  DOI：

  10.1021/jm3004009
• 作为产物：
  描述：

  2-[tert-butyl(diphenyl)silyl]oxy-1-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanone 以84的产率得到(1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol
  参考文献：
  名称：

  J. Med. Chem. 2012, 55, 4521-4525

  摘要：

  DOI：

文献信息

• Total Syntheses of a Conformationally Locked<i>North</i>-Type Methanocarba Puromycin Analogue and a Dinucleotide Derivative
  作者：Benoît Y. Michel、Peter Strazewski

  DOI：10.1002/chem.200802629

  日期：2009.6.15

  Locked in translation: Crucial insight into the ribosomal catalysis of peptide‐bond formation is expected to be gained from the target compounds, which feature conformational locking in a North‐type pucker, designed to interfere with the translation of the genetic code. The compounds were prepared from D‐ribose in 18 and 19 steps by a multi‐step synthetic route described here (see scheme).

  锁定翻译：可以从目标化合物中获得对肽键形成的核糖体催化作用的重要见解，这些化合物具有构象锁定在North- type pucker中的功能，旨在干扰遗传密码的翻译。这些化合物是由D-核糖按照此处所述的多步合成路线分18步和19步制备的（请参见方案）。
• Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides:  Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Byul Nae Yoo、Jeong A Lee、Dae Hong Shin、Lak Shin Jeong

  DOI：10.1021/jo0356762

  日期：2004.4.1

  The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.
• Synthesis of (−)-neplanocin A with the highest overall yield via an efficient Mitsunobu coupling
  作者：Benoît Y. Michel、Peter Strazewski

  DOI：10.1016/j.tet.2007.06.100

  日期：2007.9

  Neplanocin A was synthesized in very high isolated yield and purity, in 10 steps from D-ribose via an efficient Mitsunobu coupling using N-6-bis-Boc-protected adenine. In fact, this synthesis is a short pathway to enantiopure neplanocin A giving the highest published overall yield. (C) 2007 Elsevier Ltd. All rights reserved.
• Fluorocyclopentenyl-cytosine with Broad Spectrum and Potent Antitumor Activity
  作者：Won Jun Choi、Hwa-Jin Chung、Girish Chandra、Varughese Alexander、Long Xuan Zhao、Hyuk Woo Lee、Akshata Nayak、Mahesh S. Majik、Hea Ok Kim、Jin-Hee Kim、Young B. Lee、Chang H. Ahn、Sang Kook Lee、Lak Shin Jeong

  DOI：10.1021/jm3004009

  日期：2012.5.10

  On the basis of the potent biological activity of cyclopentenyl-pyrimidines, fluorocyclopentenyl-pyrimidines were designed and synthesized from D-ribose. Among these, the cytosine derivative 5a showed highly potent antigrowth effects in a broad range of tumor cell lines and very potent antitumor activity in a nude mouse tumor xenograft model implanted with A549 human lung cancer cells. However, its 2'-deoxycytidine derivative 5b did not show any antigrowth effects, indicating that 2'-hydroxyl group is essential for the biological activity.
• J. Med. Chem. 2012, 55, 4521-4525
  作者：

  DOI：——

  日期：——