dimethyl (1R,8S,9R)-4-hydroxy-8-methylthio-11,12-dioxatricyclo[7.2.1.0^2,71]dodeca-2(7),3,5-triene-3,5-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl (1R,8S,9R)-4-hydroxy-8-methylthio-11,12-dioxatricyclo[7.2.1.0^2,71]dodeca-2(7),3,5-triene-3,5-dicarboxylate
• 英文别名: dimethyl (1R,8S,9R)-4-hydroxy-8-methylsulfanyl-11,12-dioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene-3,5-dicarboxylate
• 化学式: C₁₅H₁₆O₇S
• 分子量: 340.354
• InChiKey: WRBOZWFUFJHOOS-IPZIOGDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 (Z)-1,6-anhydro-3-deoxy-4-methylsulfanyl-3-[(methylsulfanyl)methylene]-β-D-erythro-hexopyranos-2-ulose 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到dimethyl (1R,8S,9R)-4-hydroxy-8-methylthio-11,12-dioxatricyclo[7.2.1.0^2,71]dodeca-2(7),3,5-triene-3,5-dicarboxylate
  参考文献：
  名称：

  SYNTHESIS OF ANELLATED ANHYDROPYRANOSES ON THE BASIS OF 1,6-ANHYDRO-3-DEOXY-4-METHYLSULFANYL-3-[(METHYLSULFANYL)METHYLENE]-β-D-ERYTHRO-HEXOPYRANOS-2-ULOSE

  摘要：

  (Z)-1,6-Anhydro-3-deoxy-4-methylsulfanyl-3-[(methylsulfanyl)methylene]-beta -D-etythro-hexopyranos-2-ulose (1) reacted with diethyl malonate, 1,3-diketones, N-aryl-3-oxobutyramides and dialkyl 3-oxoglutarate, respectively, in the presence of potassium carbonate and crown ether to yield diethyl 2-(1,6-anhydro-4-methylsulfanyl-D-arabino-hex-2-ulopyranos-3-ylmethylene) malonate (2), 1-[(1R,2S,8S,9R)-2-hydroxy-4-methyl-8-methylthio-3,11,12-trioxatricyclo7.2. 1.0(2,7) dodeca-4,6-dien-5-yl}ethanone (3), (1R,2S,12S,13R)-2-hydroxy-12-methylthio-3,15,16-trioxatetracyclo[11.2.1. 0(2,11).0(4 9)] hexadeca-4(9),10-dien-8-one (4), (1R,8S,9R)-5-acetyl-3-aryl-8-methylthio-11,12-dioxa-3-azatricyclo-[7.2. 1.0(2,7)]dodeca-2(7),5-dien-4-ones (5,6) and dialkyl (1R,8S,9R)-4-hydroxy-8-methylthio-11,12-dioxatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-3,5-dicarboxylates (7,8), respectively.

  DOI：

  10.1081/car-100104866