(3aR,4'S,5S,6aR)-3'-benzyl-5-[(benzyloxy)methyl]-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one | 1421940-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,4'S,5S,6aR)-3'-benzyl-5-[(benzyloxy)methyl]-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one
• CAS: 1421940-21-7
• 化学式: C₂₄H₂₇NO₆
• 分子量: 425.481
• InChiKey: DMJTVVIZDVZDGV-WHLIWEHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,4'S,5S,6aR)-3'-benzyl-5-[(benzyloxy)methyl]-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one 在 sodium tetrahydroborate 、 sodium periodate 、 5%-palladium/activated carbon 、 氢气 、 苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 51.67h， 生成 ethyl (4S)-4-[(4R)-3-benzyl-4-(hydroxymethyl)-2-oxooxazolidin-4-yl]-4-hydroxybutanoate
  参考文献：
  名称：

  A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F

  摘要：

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.003
• 作为产物：
  描述：

  (3aR,4'S,5S,6aR)-3'-benzyl-5-(hydroxymethyl)-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.75h， 以98%的产率得到(3aR,4'S,5S,6aR)-3'-benzyl-5-[(benzyloxy)methyl]-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one
  参考文献：
  名称：

  A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F

  摘要：

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.003