1-((1S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-methylene-cyclopentyl)-5-methyl-1H-pyrimidine-2,4-dione | 142217-83-2

• 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: 1-((1S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-methylene-cyclopentyl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 5-methyl-1-[(1S,3R,4S)-2-methylidene-4-phenylmethoxy-3-(phenylmethoxymethyl)cyclopentyl]pyrimidine-2,4-dione
• CAS: 142217-83-2
• 化学式: C₂₆H₂₈N₂O₄
• 分子量: 432.519
• InChiKey: MUDBHZMQSIBLTD-HJOGWXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((1S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-methylene-cyclopentyl)-5-methyl-1H-pyrimidine-2,4-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到[1S-(1α,3α,4β)]-1-[4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

  摘要：

  BMS-200475, a novel carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED(50)=3 nM) with relatively low cytotoxicity (CC50=21-120 mu M). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and >99% optical purity. The enantiomer of EMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00594-x
• 作为产物：
  描述：

  (1S-反式)-2-[(苯甲氧基)甲基]-3-环戊烯-1-醇 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 甲基膦酸 、 四氯化钛 、 四丁基碘化铵 、 lithium hydride 、 sodium hydride 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-((1S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-methylene-cyclopentyl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

  摘要：

  BMS-200475, a novel carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED(50)=3 nM) with relatively low cytotoxicity (CC50=21-120 mu M). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and >99% optical purity. The enantiomer of EMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(96)00594-x

文献信息

• Hydroxymethyl(methylenecyclopentyl)Purines and Pyrimidines
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0481754B1

  公开（公告）日：1997-08-20
• US5206244A
  申请人：——

  公开号：US5206244A

  公开（公告）日：1993-04-27
• US5340816A
  申请人：——

  公开号：US5340816A

  公开（公告）日：1994-08-23
• BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro
  作者：G.S. Bisacchi、S.T. Chao、C. Bachard、J.P. Daris、S. Innaimo、G.A. Jacobs、O. Kocy、P. Lapointe、A. Martel、Z. Merchant、W.A. Slusarchyk、J.E. Sundeen、M.G. Young、R. Colonno、R. Zahler

  DOI：10.1016/s0960-894x(96)00594-x

  日期：1997.1

  BMS-200475, a novel carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED(50)=3 nM) with relatively low cytotoxicity (CC50=21-120 mu M). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and >99% optical purity. The enantiomer of EMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active. (C) 1997, Elsevier Science Ltd.