4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)butanal | 238736-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)butanal
• 英文别名: 4-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butanal
• CAS: 238736-38-4
• 化学式: C₃₈H₄₂O₆
• 分子量: 594.748
• InChiKey: SRBHHIXFLXBVAS-LKALLAANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)butanal 、 偶氮二甲酸二苄酯 在 L-脯氨酸 、 sodium tetrahydroborate 作用下， 以 乙腈 、 乙醇 为溶剂， 以61%的产率得到
  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：

  4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)butan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以100%的产率得到4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)butanal
  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

• A novel case of 1,3-asymmetric induction in rhodium-catalyzed hydroformylation of an allylic double bond using perbenzylated C-glucosides as chiral directors
  作者：Raffaello Lazzaroni、Silvia Rocchiccioli、Anna Iuliano、Laura Cipolla、Francesco Nicotra

  DOI：10.1016/j.tetasy.2005.09.030

  日期：2005.11

  1 -(2', 3',4', 6'-Tetra-O-benzyl-alpha-D-glucopyranosyl)-2-propenene and 1-(2',3',4',6' -tetra-O-benzyl-beta-D-glucopyranosyl)-2-propene 1b were hydroformylated at different temperatures affording linear and branched aldehydes in either a 1:1 or 2:1 regioisomeric ratio, depending on the stereochemistry of the starting substrate. The diastereoisomeric ratio of the branched isomer depended on the reaction temperature as well as the alkene structure, the highest value (85:15) being obtained in the case of hydroformylation of the alpha-isomer at 0 degrees C. (c) 2005 Elsevier Ltd. All rights reserved.