tert-butyl (4S,5S)-5-hydroxy-2-methyl-7-oxoicosan-4-ylcarbamate | 1040740-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (4S,5S)-5-hydroxy-2-methyl-7-oxoicosan-4-ylcarbamate
• 英文别名: tert-butyl N-[(4S,5S)-5-hydroxy-2-methyl-7-oxoicosan-4-yl]carbamate
• CAS: 1040740-97-3
• 化学式: C₂₆H₅₁NO₄
• 分子量: 441.695
• InChiKey: VLUZUEWALSYHTQ-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5S)-5-hydroxy-2-methyl-7-oxoicosan-4-ylcarbamate 在 camphor-10-sulfonic acid 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 反应 432.0h， 生成 tert-butyl (4S,5S,7R)-5,7-dihydroxy-2-methylicosan-4-ylcarbamate 、 tert-butyl (4S,5S,7S)-5,7-dihydroxy-2-methylicosan-4-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
• 作为产物：
  描述：

  tert-butyl (4S,5S)-5-hydroxy-2-methyl-7-methylenicosan-4-ylcarbamate 在 四氧化锇 、 sodium periodate 作用下， 以 乙醚 、 水 为溶剂， 反应 20.0h， 生成 tert-butyl (4S,5S)-5-hydroxy-2-methyl-7-oxoicosan-4-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.