tert-butyl benzyl((R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate | 949490-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl benzyl((R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate
• CAS: 949490-35-1
• 化学式: C₂₁H₃₁NO₅
• 分子量: 377.481
• InChiKey: YHXVOQGGTKCVLF-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl benzyl((R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate 、 对硝基苯基氯甲酸酯 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以77%的产率得到(2S,3S,4R)-4-(N-benzyl-N-tert-butyloxycarbonylamino)-1-O-carbamoyl-2,3-dioxyisopropylidene-hex-5-en
  参考文献：
  名称：

  New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon

  摘要：

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.002
• 作为产物：
  描述：

  (2S,3S,4R)-4-(N-benzyl-N-tert-butoxycarbonylamino)-1-tert-butyldiphenylsilyloxy-2,3-dioxyisopropylidene-hex-5-en 在 四丁基氟化铵 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到tert-butyl benzyl((R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate
  参考文献：
  名称：

  New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon

  摘要：

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.002