L-trehalose | 562834-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-trehalose
• 英文别名: L-Glc(a1-1a)L-Glc；(2S,3R,4R,5S,6S)-2-(hydroxymethyl)-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 562834-27-9
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: HDTRYLNUVZCQOY-CAPXFGMSSA-N

物化性质

• 沸点：
  675.4±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 L-trehalose 以 吡啶 为溶剂， 生成 octa-O-acetyl-L-trehalose
  参考文献：
  名称：

  Synthesis of l-trehalose and observations on isomer and by-product formation

  摘要：

  With a view to gaining evidence on the mechanism by which D-trehalose is able to stabilise biomolecules towards dehydration (anhydrobiosis) and heat, L-trehalose has been prepared in order to allow comparative studies to be made. Little change can be induced in the ratio of the alpha,alpha-, alpha,beta-1,1'-stereoisomers of the disaccharide formed from 2,3,4,6-tetra-O-benzyl-L-glucose by using different reaction procedures and by varying the reaction conditions. Benzyl 2,3,4,6-tetra-O-benzyl alpha- and beta-L-glucopyranoside are by-products in the trimethylsilyl trifluoromethanesulphonate mediated formation of the 1,1'-linked disaccharides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00043-0
• 作为产物：
  描述：

  octa-O-benzyl-L-trehalose 在 palladium on activated charcoal 溶剂黄146 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 288.0h， 以87%的产率得到L-trehalose
  参考文献：
  名称：

  Synthesis of l-trehalose and observations on isomer and by-product formation

  摘要：

  With a view to gaining evidence on the mechanism by which D-trehalose is able to stabilise biomolecules towards dehydration (anhydrobiosis) and heat, L-trehalose has been prepared in order to allow comparative studies to be made. Little change can be induced in the ratio of the alpha,alpha-, alpha,beta-1,1'-stereoisomers of the disaccharide formed from 2,3,4,6-tetra-O-benzyl-L-glucose by using different reaction procedures and by varying the reaction conditions. Benzyl 2,3,4,6-tetra-O-benzyl alpha- and beta-L-glucopyranoside are by-products in the trimethylsilyl trifluoromethanesulphonate mediated formation of the 1,1'-linked disaccharides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00043-0