3β-azido-4β-fluoro-5β-benzyloxymethyl-1α,2α-isopropylidenedioxycyclopentane | 869792-62-1

• 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: 3β-azido-4β-fluoro-5β-benzyloxymethyl-1α,2α-isopropylidenedioxycyclopentane
• 英文别名: (3aS,4S,5R,6R,6aR)-4-azido-5-fluoro-2,2-dimethyl-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole
• CAS: 869792-62-1
• 化学式: C₁₆H₂₀FN₃O₃
• 分子量: 321.352
• InChiKey: KUXJOZIPILSNSO-JARUQAPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3β-azido-4β-fluoro-5β-benzyloxymethyl-1α,2α-isopropylidenedioxycyclopentane 在 Lindlar's catalyst 氨 、 氢气 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 生成 3β-(6-aminopurin-9-yl)-4β-fluoro-5β-benzyloxymethyl-1α,2α-isopropylidenedioxycyclopentane
  参考文献：
  名称：

  6'-β-氟阿霉素，6'-β-氟-5'-阿霉素和阿霉素的手性合成

  摘要：

  在C-6'位置取代的碳环核苷受到越来越多的关注。缺乏对生物学上有希望的6'-β-氟代阿霉素霉素的手性合成可及性。描述了其制备和5'-nor类似物的制备。一路走来，一种新的阿霉素霉素的方法作为必需的结构证明的产物出现了。

  DOI：

  10.1016/j.tetlet.2005.08.163
• 作为产物：
  描述：

  Trifluoro-methanesulfonic acid (3aR,4R,5R,6S,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester 生成 3β-azido-4β-fluoro-5β-benzyloxymethyl-1α,2α-isopropylidenedioxycyclopentane
  参考文献：
  名称：

  MADHAVAN, BINDU G. V.;MCGEE, DANNY P. C.;RYDZEWSKI, ROBERT M.;BOEHME, RIC+, J. MED. CHEM., 31,(1988) N 9, C. 1798-1804

  摘要：

  DOI：

文献信息

• Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04605659A1

  公开（公告）日：1986-08-12

  Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.

  4-取代-5-羟甲基-1,2-环戊二醇或在3位位置被各种杂环基团取代的1-环戊醇可用作抗病毒剂。
• Synthesis and antiviral evaluation of 6'-substituted aristeromycins: potential mechanism-based inhibitors of S-adenosylhomocysteine hydrolase
  作者：G. V. Bindu Madhavan、Danny P. C. McGee、Robert M. Rydzewski、Richard Boehme、John C. Martin、Ernest J. Prisbe

  DOI：10.1021/jm00117a021

  日期：1988.9

  New carbocyclic adenosine analogues substituted at the 6'-position with fluorine, hydroxyl, methylene, or hydroxymethyl have been synthesized as potential mechanism-based inhibitors of S-adenosylhomocysteine (AdoHcy) hydrolase. The synthetic routes began with a functionalized (+/-)-azidocyclopentane 2, which was elaborated to the adenosine analogue, or with functionalized cyclopentane epoxides 11, 20, and 27, which were opened directly with adenine in the presence of base. The 6' alpha-fluoro, 6' beta-fluoro, and 6'-methylene carbocyclic adenosine analogues were potent inhibitors of AdoHcy hydrolase. None of the compounds displayed significant activity against herpes simplex virus type 1 or type 2, but several demonstrated potent inhibition of vaccinia virus replication.