8,9-dihydro-10-deoxymethynolide | 1099832-65-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 8,9-dihydro-10-deoxymethynolide
• 英文别名: 8.8-dihydro-10-deoxymethynolide；(3R,4S,5S,7R,11R,12R)-12-ethyl-4-hydroxy-3,5,7,11-tetramethyl-oxacyclododecane-2,8-dione
• CAS: 1099832-65-1
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: WCOXOPLZBQMWMX-JRKAUPQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2S,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 、 8,9-dihydro-10-deoxymethynolide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到(3R,4S,5S,7R,11R,12R)-12-ethyl-3,5,7,11-tetramethyl-4-(((2R,6R)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)oxacyclododecane-2,8-dione
  参考文献：
  名称：

  A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

  摘要：

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

  DOI：

  10.1021/ol102144g
• 作为产物：
  描述：

  10-去氧微甘菊内酯 在 2-硝基苯磺酰肼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以95%的产率得到8,9-dihydro-10-deoxymethynolide
  参考文献：
  名称：

  A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity

  摘要：

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.

  DOI：

  10.1021/ol102144g

文献信息

• Exploiting the natural metabolic diversity of Streptomyces venezuelae to generate unusual reduced macrolides
  作者：Je Won Park、Hong-Se Oh、Won Seok Jung、Sung Ryeol Park、Ah Reum Han、Yeon-Hee Ban、Eun Ji Kim、Han-Young Kang、Yeo Joon Yoon

  DOI：10.1039/b814603a

  日期：——

  An unusual set of reduced macrolide antibiotics was discovered by combination of organic synthesis and a biosynthetic approach using the unique metabolic diversity of Streptomyces venezuelae; two unnatural 16-membered ring macrolides are also created by employing this bio-catalyst.

  通过有机合成和生物合成方法结合委内瑞拉链霉菌独特的代谢多样性，发现了一套不同寻常的还原性大环内酯类抗生素。通过使用这种生物催化剂，还产生了两个非天然的16元环大环内酯类化合物。
• A De Novo Approach to the Synthesis of Glycosylated Methymycin Analogues with Structural and Stereochemical Diversity
  作者：Svetlana A. Borisova、Sanjeeva R. Guppi、Hak Joong Kim、Bulan Wu、John H. Penn、Hung-wen Liu、George A. O’Doherty

  DOI：10.1021/ol102144g

  日期：2010.11.19

  A divergent and highly stereoselective route to 11 glycosylated methymycin analogues has been developed. The key to the success of this method was the iterative use of the Pd-catalyzed glycosylation reaction and postglycosylation transformation. This unique application of Pd-catalyzed glycosylation demonstrates the breath of alpha/beta- and D/L-glycosylation of macrolides that can be efficiently prepared using a de novo asymmetric approach to the carbohydrate portion.