Tert-butyl (4S)-4-hexadecanoyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 207509-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: Tert-butyl (4S)-4-hexadecanoyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 207509-04-4
• 化学式: C₂₆H₄₉NO₄
• 分子量: 439.679
• InChiKey: SMAWUTBOJBVYFQ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl (4S)-4-hexadecanoyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(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 吗啉 、 lithium hydroxide 、 四(三苯基膦)钯 、 sodium hydride 、 对甲苯磺酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.5h， 生成 Tert-butyl (4S)-4-hexadecanoyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  A Synthesis of d-erythro- and l-threo-Sphingosine and Sphinganine Diastereomers via the Biomimetic Precursor 3-Ketosphinganine

  摘要：

  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.

  DOI：

  10.1021/jo980003i

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.
• A concise route to d-erythro-sphingosine from N-Boc-l-serine derivatives via sulfoxide or sulfone intermediates
  作者：Jiong Chun、Guoqing Li、Hoe-Sup Byun、Robert Bittman

  DOI：10.1016/s0040-4039(01)02145-1

  日期：2002.1

  Sulfoxide and sulfone intermediates 7 and 15, respectively, were employed to synthesize synthons 3 and 4, which are readily converted to the naturally occurring (2S,3R,4(E))-sphingosine 1 and (2S,3R)-sphinganine 2. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.