(2R,4aR,6S,7R,8R,8aS)-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | 511274-47-8

• 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)-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 511274-47-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: FJNHUVZYONYQSJ-WVXCVLBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 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)-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 在 D(+)-10-樟脑磺酸 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 5.0h， 生成 (2R,3R,4S,5S,6S)-2-(hydroxymethyl)-4,5-dimethoxy-6-phenyloxan-3-ol
  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 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.5h， 生成 (2R,4aR,6S,7R,8R,8aS)-2,6-diphenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
  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。
• Regioselective Deacetylation of Peracetylated Deoxy-<i>C</i>-glycopyranosides by Boron Trichloride (BCl₃)
  作者：Shuangyuan Chen、Feifei Wei、Xinqiang Cheng、Ying Luo、Fancui Meng、Yuanwen Zhang、Wenqian Huang、Jun Lv、Hong Pan、Qingqing Wu、Guilong Zhao

  DOI：10.1021/acs.joc.4c00026

  日期：2024.4.5

  for regioselective deacetylation at sugar 3-OH of peracetylated 6-deoxy-C-glucopyranosides mediated by BCl3 was developed. The approach could be extended to other sugar-derived 6-deoxy-C-glycopyranosides, such as those derived from mannose, galactose, and rhamnose, with deacetylation occurring at varied sugar hydroxyl groups, and further extended to 4-deoxy-C-glucopyranosides with deacetylation occurring

  开发了由 BCl 3介导的全乙酰化 6-脱氧-C-吡喃葡萄糖苷的糖 3-OH 区域选择性脱乙酰化的通用方法。该方法可以扩展到其他糖衍生的 6-脱氧-C-吡喃葡萄糖苷，例如衍生自甘露糖、半乳糖和鼠李糖的那些，在不同的糖羟基上发生脱乙酰化，并进一步扩展到 4-脱氧-C-吡喃葡萄糖苷糖3-OH处发生脱乙酰化。该方法将能够获得具有合成挑战性的碳水化合物衍生物。提出了区域选择性的可能机制。
• 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.