tert-butyl (2S,3S)-1-(benzyloxy)-3-hydroxy-5-methylenoctadecan-2-ylcarbamate | 1040740-81-5

• 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: tert-butyl (2S,3S)-1-(benzyloxy)-3-hydroxy-5-methylenoctadecan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S,3S)-3-hydroxy-5-methylidene-1-phenylmethoxyoctadecan-2-yl]carbamate
• CAS: 1040740-81-5
• 化学式: C₃₁H₅₃NO₄
• 分子量: 503.766
• InChiKey: RNKMSSOQOLMBBU-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  trichloro(2-methylenepentadecyl)stannane 、 (S)-2-(t-butoxycarbonylamino)-3-phenylmetoxy-1-propanal 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (2S,3R)-1-(benzyloxy)-3-hydroxy-5-methylenoctadecan-2-ylcarbamate 、 tert-butyl (2S,3S)-1-(benzyloxy)-3-hydroxy-5-methylenoctadecan-2-ylcarbamate
  参考文献：
  名称：

  An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols

  摘要：

  AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.049

文献信息

• An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols
  作者：Luiz C. Dias、Juliana Fattori、Carla C. Perez、Vanda M. de Oliveira、Andrea M. Aguilar

  DOI：10.1016/j.tet.2008.04.049

  日期：2008.6

  AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.