tert-butyl (4S)-2,2-dimethyl-4-(3-oxo-3-prop-2-enoxypropanoyl)-1,3-oxazolidine-3-carboxylate | 207509-03-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tert-butyl (4S)-2,2-dimethyl-4-(3-oxo-3-prop-2-enoxypropanoyl)-1,3-oxazolidine-3-carboxylate
• CAS: 207509-03-3
• 化学式: C₁₆H₂₅NO₆
• 分子量: 327.378
• InChiKey: CEWKYOUPBZPLTA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-2,2-dimethyl-4-(3-oxo-3-prop-2-enoxypropanoyl)-1,3-oxazolidine-3-carboxylate 在 吗啉 、 sodium tetrahydroborate 、 tris(triphenylphosphano)palladium 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (2S,3R)-2-[(tert-butoxycarbonyl)amino]-1,2-O-N-isopropylideneoctadecane-1,3-diol
  参考文献：
  名称：

  Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine

  摘要：

  D-erythro-sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in goad overall yields (approximate to 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00733-3
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 lithium hydroxide 、 对甲苯磺酸 、 N,N'-羰基二咪唑 作用下， 生成 tert-butyl (4S)-2,2-dimethyl-4-(3-oxo-3-prop-2-enoxypropanoyl)-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine

  摘要：

  D-erythro-sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in goad overall yields (approximate to 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00733-3

文献信息

• A Synthesis of <scp>d</scp>-<i>erythro</i>- and <scp>l</scp>-<i>threo</i>-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo980003i

  日期：1998.6.1

  The four stereoisomers of sphingosine and sphinganine can be produced in protected form by a short, convergent, biomimetic synthesis from serine. Yields are good (26-38% overall from commercially available serine derivatives), and the stereoselectivities are excellent (>92% de, >95% eel. Several sphingosine L-threo-sphingosine analogues with modified, functionalized tails were prepared to demonstrate the versatility of the method.
• Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4039(98)00733-3

  日期：1998.6

  D-erythro-sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in goad overall yields (approximate to 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee). (C) 1998 Elsevier Science Ltd. All rights reserved.