benzyl N-[(1S)-2-hydroxy-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]-N-(phenylmethoxycarbonylamino)carbamate | 1069116-51-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl N-[(1S)-2-hydroxy-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]-N-(phenylmethoxycarbonylamino)carbamate
• CAS: 1069116-51-3
• 化学式: C₅₂H₅₄N₂O₁₀
• 分子量: 867.008
• InChiKey: YMNWALRYTFBIMF-ILIXGMQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  64
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl N-[(1S)-2-hydroxy-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]-N-(phenylmethoxycarbonylamino)carbamate 在 氢气 、 镍 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  General Synthesis of C-Glycosyl Amino Acids via Proline-Catalyzed Direct Electrophilic α-Amination of C-Glycosylalkyl Aldehydes

  摘要：

  Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de > 95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.

  DOI：

  10.1021/ol801685x
• 作为产物：
  描述：

  偶氮二甲酸二苄酯 、 (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal 在 L-脯氨酸 、 sodium tetrahydroborate 作用下， 以 乙腈 、 乙醇 为溶剂， 反应 0.25h， 以80%的产率得到benzyl N-[(1S)-2-hydroxy-1-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethyl]-N-(phenylmethoxycarbonylamino)carbamate
  参考文献：
  名称：

  General Synthesis of C-Glycosyl Amino Acids via Proline-Catalyzed Direct Electrophilic α-Amination of C-Glycosylalkyl Aldehydes

  摘要：

  Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de > 95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.

  DOI：

  10.1021/ol801685x

文献信息

• General Synthesis of <i>C</i>-Glycosyl Amino Acids via Proline-Catalyzed Direct Electrophilic α-Amination of <i>C</i>-Glycosylalkyl Aldehydes
  作者：Andrea Nuzzi、Alessandro Massi、Alessandro Dondoni

  DOI：10.1021/ol801685x

  日期：2008.10.16

  Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de > 95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.