(1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol | 681853-99-6

• 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: (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol
• CAS: 681853-99-6
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: DCRRLTHZZHSUDW-OFQRWUPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 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 为溶剂， 反应 66.75h， 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：

  (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 草酰氯 、 二正丁基氧化锡 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 69.0h， 生成 (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol
  参考文献：
  名称：

  Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides:  Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

  摘要：

  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.

  DOI：

  10.1021/jo0356762

文献信息

• STEREOSELECTIVE SYNTHESIS OF 3-HYDROXYMETHYL-D-CYCLOPENTENONE, THE VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Young Mi Ko、Hye Jin Kim、Jeong A. Lee、Kang Man Lee、Mi Kyung Yun、Dae Hong Shin、Moon Woo Chun、Yhun Y. Sheen、Kilhyoun Kim、Lak Shin Jeong

  DOI：10.1081/ncn-200061832

  日期：2005.4.1

  The preparative and stereoselective synthesis (45 - 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.
• J. Med. Chem. 2012, 55, 4521-4525
  作者：

  DOI：——

  日期：——