[(4aR,6R,7S,8S,8aR)-8-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(9-methoxy-9-oxononoxy)spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] benzoate | 701937-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4aR,6R,7S,8S,8aR)-8-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(9-methoxy-9-oxononoxy)spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] benzoate
• CAS: 701937-04-4
• 化学式: C₅₆H₇₀O₁₄
• 分子量: 967.163
• InChiKey: BEVRXDKVEGIJCB-MKNQEMAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  70
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 、 [(4aR,6R,7S,8S,8aR)-8-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(9-methoxy-9-oxononoxy)spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] benzoate 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 xylene 为溶剂， 反应 7.5h， 以77%的产率得到
  参考文献：
  名称：

  Accelerated glycosylation under frozen conditions

  摘要：

  O-Glycosylations using thiomethyl glycosides as donors were compared under both frozen and unfrozen conditions. In the presence of MeOTf as a promoter, enormous rate acceleration was observed when the glycosylation was conducted in p-xylene below its freezing point. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.100
• 作为产物：
  描述：

  ((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 在 2,6-二叔丁基-4-甲基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 11.5h， 生成 [(4aR,6R,7S,8S,8aR)-8-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-(9-methoxy-9-oxononoxy)spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] benzoate
  参考文献：
  名称：

  Accelerated glycosylation under frozen conditions

  摘要：

  O-Glycosylations using thiomethyl glycosides as donors were compared under both frozen and unfrozen conditions. In the presence of MeOTf as a promoter, enormous rate acceleration was observed when the glycosylation was conducted in p-xylene below its freezing point. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.100