(2R,4aR,6S,7S,8R,8aR)-7,8-dimethoxy-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine | 511274-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7S,8R,8aR)-7,8-dimethoxy-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 511274-41-2
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: ZIGZMEZHXMZEPZ-ZWJPJJENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7S,8R,8aR)-7,8-dimethoxy-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 在 吡啶 、 Grubbs catalyst first generation 、 D(+)-10-樟脑磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 152.0h， 生成 (1R,14R,16S,17S,18R)-17,18-Dimethoxy-16-phenyl-2,7,12,15-tetraoxa-tricyclo[12.4.0.0^6,8]octadecane-3,11-dione
  参考文献：
  名称：

  A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity

  摘要：

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

  DOI：

  10.1021/jo051021k
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 D(+)-10-樟脑磺酸 、 氢溴酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.5h， 生成 (2R,4aR,6S,7S,8R,8aR)-7,8-dimethoxy-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity

  摘要：

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

  DOI：

  10.1021/jo051021k

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。
• Preparation and use of carbohydrate-based ring structures with antimicrobial and cytostatic activity
  申请人：Kemin Pharma Europe

  公开号：EP2168972A2

  公开（公告）日：2010-03-31

  A compound of the formula : wherein R1 is -H, -SPh, -Ph, -allyl or -benzyl; R2 is -H, -Et, -allyl, -Me or -benzyl; R3 is -H, -Et, -Me, -allyl or -benzyl; and R4 and R5 are both -OH or R4 and R5 together form a ring and are -OCH(Ph)O- ; or a pharmaceutically active derivative thereof. Pharmaceutical compositions comprising the above compounds and their use in therapy are also provided.

  式中的化合物： 其中 R1 是-H、-SPh、-Ph、-烯丙基或-苄基； R2 是-H、-Et、-烯丙基、-Me 或-苄基 R3 是-H、-Et、-Me、-烯丙基或-苄基；以及 R4 和 R5 都是-OH，或者 R4 和 R5 共同形成一个环，并且是-OCH(Ph)O-； 或其药用活性衍生物。 还提供了包含上述化合物的药物组合物及其在治疗中的用途。
• US7534871B2
  申请人：——

  公开号：US7534871B2

  公开（公告）日：2009-05-19
• A Convergent Ring-Closing Metathesis Approach to Carbohydrate-Based Macrolides with Potential Antibiotic Activity
  作者：Petra Blom、Bart Ruttens、Steven Van Hoof、Idzi Hubrecht、Johan Van der Eycken、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove

  DOI：10.1021/jo051021k

  日期：2005.11.1

  An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against, Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.
• 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.