(3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one | 864445-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one
• CAS: 864445-03-4
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: OPMOEIXOYFLVKN-LISHHDFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one 、 lithium methanolate 以 甲醇 为溶剂， 反应 0.08h， 以90%的产率得到(2S)-methyl 3,7-anhydro-2-phenyl-5-O-methyl-8-deoxy-α-D-altro-octitolate
  参考文献：
  名称：

  Synthesis of the Branched C-Glycoside Substructure of Altromycin B

  摘要：

  [GRAPHICS]Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).

  DOI：

  10.1021/ol050975u
• 作为产物：
  描述：

  (S)-[(2S,3S,4R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl]-hydroxy-phenyl-acetic acid methyl ester 在 四丁基氟化铵 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 54.5h， 生成 (3S,3aS,5R,6R,7R,7aS)-3,6-Dihydroxy-7-methoxy-5-methyl-3-phenyl-hexahydro-furo[3,2-b]pyran-2-one
  参考文献：
  名称：

  Synthesis of the Branched C-Glycoside Substructure of Altromycin B

  摘要：

  [GRAPHICS]Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b).

  DOI：

  10.1021/ol050975u