(4R,5R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-1-[(3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]-5,7-bis(phenylmethoxy)heptan-2-one | 138061-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-1-[(3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]-5,7-bis(phenylmethoxy)heptan-2-one
• CAS: 138061-69-5；138230-73-6
• 化学式: C₄₇H₆₂O₉Si
• 分子量: 799.089
• InChiKey: NMISJNJVBUBTPB-KROZZKARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.68
• 重原子数：
  57.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4R,5R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-1-[(3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]-5,7-bis(phenylmethoxy)heptan-2-one 在 偶氮二异丁腈 、 四甲基乙二胺 、 三氟化硼乙醚 、 四丁基氟化铵 、 氨 、 三正丁基氢锡 、 三乙胺 、 magnesium bromide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 苯 为溶剂， 反应 15.5h， 生成 (2S,3S,5S,6R)-2-[[(3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]methyl]-3-[[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-one
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019
• 作为产物：
  描述：

  1,3-O-Dibenzyl-2-O-(tert-butyldimethylsilyl)threitol 在 lithium hexamethyldisilazane 作用下， 反应 0.67h， 生成 (4R,5R,6R)-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-1-[(3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl]-5,7-bis(phenylmethoxy)heptan-2-one
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019