(2R,4aR,6S,7R,8R,8aS)-2-naphthalen-2-yl-6-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | 850313-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7R,8R,8aS)-2-naphthalen-2-yl-6-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 850313-78-9
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: VCSOJGYABOFPAQ-FHJOOOADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8R,8aS)-2-naphthalen-2-yl-6-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 、 碘甲烷 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 15.5h， 以93%的产率得到(2R,4aR,6S,7S,8R,8aR)-7,8-Dimethoxy-2-naphthalen-2-yl-6-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae

  摘要：

  用于治疗由疱疹病毒科感染引起的感染，特别是巨细胞病毒的双环碳水化合物。该发明包括新型双环碳水化合物，其通用结构如下：其中R1为-Bn或-Ph；R2和R3为-烷基，-芳基，-烯丙基或-H；R4和R5形成一个环，可以是-CH(Ph)-或-CH(芳基)-，X可以是O，N或S。

  公开号：

  US20050090452A1
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 在 camphor-10-sulfonic acid 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 21.0h， 生成 (2R,4aR,6S,7R,8R,8aS)-2-naphthalen-2-yl-6-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
  参考文献：
  名称：

  Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals

  摘要：

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.048

文献信息

• Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae
  申请人：Sas Benedikt

  公开号：US20050090452A1

  公开（公告）日：2005-04-28

  Bicyclic carbohydrates for the treatment of infections caused by herpseviridae, and in particular cytomegalovirus. The invention consists of the novel bicyclic carbohydrates the generic structure of which is: wherein R 1 is either -Bn or -Ph; R 2 and R 3 are either -alkyl, -aryl, -allyl, or —H; R 4 and R 5 form a ring and are either —CH(Ph)- or —CH(aryl)- and X is either O, N or S.

  用于治疗由疱疹病毒科感染引起的感染，特别是巨细胞病毒的双环碳水化合物。该发明包括新型双环碳水化合物，其通用结构如下：其中R1为-Bn或-Ph；R2和R3为-烷基，-芳基，-烯丙基或-H；R4和R5形成一个环，可以是-CH(Ph)-或-CH(芳基)-，X可以是O，N或S。
• Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals
  作者：Steven Van Hoof、Bart Ruttens、Idzi Hubrecht、Gert Smans、Petra Blom、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove、Johan Van der Eycken

  DOI：10.1016/j.bmcl.2005.12.048

  日期：2006.3

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.