(+)-(1S,2R,3R,6R)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate | 168921-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1S,2R,3R,6R)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate
• CAS: 168921-98-0
• 化学式: C₂₄H₃₄O₁₄
• 分子量: 546.526
• InChiKey: RYFHVZVTOUETMG-XBSJZXHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  187.26
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R,3R,6R)-2-hydroxy-6-methoxy-4-oxo-3-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>cyclohexyl acetate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-((1S,2R,3S,4R,6S)-3-acetoxy-2,6-dihydroxy-4-methoxy-cyclohexylmethyl)-6-acetoxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  碳糖的α-C-半乳糖苷的合成：一类新型的二糖模拟物

  摘要：

  （+）-（1 S，2 S，3 R，4 R，5 R）-2-[（2'，3'，4'，6'-四-O-乙酰基-α-D-吡喃半乳糖基）甲基源自于D-半乳糖和（1 R，4 R）-7-氧杂双环[2.2.1]-庚-5-en-2-one的] -5-甲基-氧环己基-1,3,4-三乙酸三乙酸酯。

  DOI：

  10.1016/0040-4039(95)00548-q
• 作为产物：
  描述：

  (+)-(1R,2S,3S,4R,6R)-3-endo-methoxy-5-oxo-6-endo-<(2',3',4',6'-tetra-O-acetyl-α-D-galactopyranosyl)methyl>-7-oxabicyclo<2.2.1>hept-2-endo-yl acetate 在 三乙胺 作用下， 以 异丙醇 为溶剂， 以28%的产率得到(+)-(1S,2R,3R,6R)-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：

  碳糖的α-C-半乳糖苷的合成：一类新型的二糖模拟物

  摘要：

  （+）-（1 S，2 S，3 R，4 R，5 R）-2-[（2'，3'，4'，6'-四-O-乙酰基-α-D-吡喃半乳糖基）甲基源自于D-半乳糖和（1 R，4 R）-7-氧杂双环[2.2.1]-庚-5-en-2-one的] -5-甲基-氧环己基-1,3,4-三乙酸三乙酸酯。

  DOI：

  10.1016/0040-4039(95)00548-q

文献信息

• Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-.alpha.-Galactosides of Carbapentopyranoses
  作者：Janine Cossy、Jean-Luc Ranaivosata、Veronique Bellosta、Jacek Ancerewicz、Rafael Ferritto、Pierre Vogel

  DOI：10.1021/jo00131a007

  日期：1995.12

  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).