(+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate | 173243-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate
• 英文别名: [(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-[[(1S,2S,3R,4S)-3-acetyloxy-2-hydroxy-4-methoxy-6-oxocyclohexyl]methyl]oxan-2-yl]methyl acetate
• CAS: 173243-07-7
• 化学式: C₂₄H₃₄O₁₄
• 分子量: 546.526
• InChiKey: RYFHVZVTOUETMG-RCOZCXGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  187
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 生成 (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexa-1,3,4-triyl triacetate 、 (1S,2R,3S,4S,5S)-5-methoxy-2-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexa-1,3,4-triyl triacetate
  参考文献：
  名称：

  Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-.alpha.-Galactosides of Carbapentopyranoses

  摘要：

  Photoinduced electron transfer from Et(3)N to 7-oxabicyclo[2.2.1]heptan-2-ones can generate the corresponding 3-hydroxycyclohexanone derivatives. The method has been applied to the synthesis of C-alpha-D-galactopyranosides of carbapentopyranoses. Radical alpha-D-galactosidation of (+/-)-(1RS,4RS,5RS, 6RS)-6-endo-methoxy-3-methylidene-5-exo-(phenylseleno)-7-oxabicyclo[2.2.l]hept-2-one ((+)-51) followed by seleno-Pummerer rearrangement and reduction with Bu(3)SnH gave (+)- (1R,2S,3S,4R,6R)-((+)-58) and (+)-(1S,2R,3R,4S,6S)-3-endo-methoxy-5-oxo-6-endo-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]-7-oxabicyclo[2.2.1]hept-2-endo-yl acetate ((+)-59), which were separated by column chromatography. Irradiation (254 nn) in the presence of Et(3)N gave (+)-(1S,2R,3R,6R)-((+)-60) and (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexyl acetate (+)-61, respectively. NaBH4 reduction and acetylation provided (+)-(1S,2S,3R,4R,5R)-((+)-62) and (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexa-1,3,4-triyl triacetate ((+)-64).

  DOI：

  10.1021/jo00131a007
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium acetate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 异丙醇 为溶剂， 反应 9.0h， 生成 (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate
  参考文献：
  名称：

  Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-.alpha.-Galactosides of Carbapentopyranoses

  摘要：

  Photoinduced electron transfer from Et(3)N to 7-oxabicyclo[2.2.1]heptan-2-ones can generate the corresponding 3-hydroxycyclohexanone derivatives. The method has been applied to the synthesis of C-alpha-D-galactopyranosides of carbapentopyranoses. Radical alpha-D-galactosidation of (+/-)-(1RS,4RS,5RS, 6RS)-6-endo-methoxy-3-methylidene-5-exo-(phenylseleno)-7-oxabicyclo[2.2.l]hept-2-one ((+)-51) followed by seleno-Pummerer rearrangement and reduction with Bu(3)SnH gave (+)- (1R,2S,3S,4R,6R)-((+)-58) and (+)-(1S,2R,3R,4S,6S)-3-endo-methoxy-5-oxo-6-endo-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]-7-oxabicyclo[2.2.1]hept-2-endo-yl acetate ((+)-59), which were separated by column chromatography. Irradiation (254 nn) in the presence of Et(3)N gave (+)-(1S,2R,3R,6R)-((+)-60) and (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexyl acetate (+)-61, respectively. NaBH4 reduction and acetylation provided (+)-(1S,2S,3R,4R,5R)-((+)-62) and (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexa-1,3,4-triyl triacetate ((+)-64).

  DOI：

  10.1021/jo00131a007