2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane | 100021-14-5

• 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: 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
• 英文别名: (1α,2α,3β,4α,5α)-2,4-dihydroxy-3-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane
• CAS: 100021-14-5
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: CRZULRYGBCSFJT-HALBRFILSA-N

物化性质

• 沸点：
  416.1±35.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62.22
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以100%的产率得到(+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol
  参考文献：
  名称：

  A novel and stereospecific synthesis of (.+-.)- and (-)-aristeromycin

  摘要：

  DOI：

  10.1021/jo00358a023
• 作为产物：
  描述：

  (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以62%的产率得到2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
  参考文献：
  名称：

  A novel and stereospecific synthesis of (.+-.)- and (-)-aristeromycin

  摘要：

  DOI：

  10.1021/jo00358a023

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.
• Neighboring group effects in the regioselective cyclization of vicinal trans-1,2-bromohydrins to epoxides
  作者：Fengrui Lang、Darren J Kassab、Bruce Ganem

  DOI：10.1016/s0040-4039(98)01243-x

  日期：1998.8

  Bromocyclopentitols and amino (or amido) bromocyclopentitols having a C-Br bond trans to two different vicinal hydroxyl groups show selectivity in base-promoted epoxide formation. The role of adjacent polar substituents in directing bromohydrin cyclization is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• US4605659A
  申请人：——

  公开号：US4605659A

  公开（公告）日：1986-08-12
• US4704392A
  申请人：——

  公开号：US4704392A

  公开（公告）日：1987-11-03