methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate | 160080-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate
• CAS: 160080-76-2
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: GPZPGKAKDVDLRA-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate 在 palladium dihydroxide 、 palladium on activated charcoal sodium hydroxide 、 lithium aluminium tetrahydride 、 AcOH buffer 、 四丁基氟化铵 、 氢气 、 silver trifluoromethanesulfonate 、 sodium hydride 、 二正丁基氧化锡 、 臭氧 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成
  参考文献：
  名称：

  Design and synthesis of sialyl Lex mimetics based on carbocyclic scaffolds derived from (−) quinic acid

  摘要：

  The synthesis of sialyl Lewis(x) mimetic anologs in which the D-glucosamine, D-galactose, and sialic acid residues are replaced individually with appropriate glycomimetics is described. A computational model for predicting bioactive conformations was tested. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10077-4
• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 草酰氯 、 camphor-10-sulfonic acid 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.33h， 生成 methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Bio-inspired synthesis of rare and unnatural carbohydrates and cyclitols through strain driven epimerization

  摘要：

  通过通过对碳水化合物和环己醇进行仿生异构化，通过应变驱动的将反式-酮缩醛异构化为顺式-酮缩醛，引入了它们罕见且非自然的异构体。

  DOI：

  10.1039/c4cc00868e

文献信息

• A Class of <i>C</i><i>₂</i> and Pseudo <i>C</i><i>₂</i> Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis
  作者：Zhi-Xian Wang、Susie M. Miller、Oren P. Anderson、Yian Shi

  DOI：10.1021/jo9908849

  日期：1999.8.1

  A class of C-2 and pseudo C-2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.
• Synthesis and evaluation of 3-deoxy-D-manno-2-octulosonate-8-phosphate (KDO8P) synthase inhibitors
  作者：Hongtao Liu、Weixing Li、Choung U. Kim

  DOI：10.1016/s0960-894x(97)00232-1

  日期：1997.6
• Hepoxilins B3: Synthesis of all four stereoisomers and a glutathione adduct
  作者：Yuri Y. Belosludtsev、R.Omindine Kollah、J.R. Falck、Jorge H. Capdevila

  DOI：10.1016/s0040-4039(00)73491-5

  日期：1994.7

  Utilizing (-)-quinic acid as a differentiated bis-aldehyde chiron, both pairs of hepoxilin B-3 enantiomers and a glutathione adduct were synthesized by regiospecific functionalization of an acyclic vic-diol.
• [EN] C-GLYCOSIDES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] C-GLYCOSIDES UTILISÉS COMME AGENTS ANTI-INFLAMMATOIRES
  申请人：[en]UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2024010959A1

  公开（公告）日：2024-01-11

  Novel compounds and methods of using the compounds are provided herein. The compounds include novel carbon analogs of pyranose derivatives discovered to have Toll- like receptor 4 (Tlr4) inhibitory activity. The methods provide for treating infectious, inflammatory and post-traumatic disorders.
• Design and synthesis of sialyl Lex mimetics based on carbocyclic scaffolds derived from (−) quinic acid
  作者：Stephen Hanessian、Gurijala V. Reddy、Hoan K. Huynh、Jingwen Pan、Silvana Pedatella、Beat Ernst、Hartmuth C. Kolb

  DOI：10.1016/s0960-894x(97)10077-4

  日期：1997.11

  The synthesis of sialyl Lewis(x) mimetic anologs in which the D-glucosamine, D-galactose, and sialic acid residues are replaced individually with appropriate glycomimetics is described. A computational model for predicting bioactive conformations was tested. (C) 1997 Elsevier Science Ltd.