trehalose | 162678-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trehalose
• 英文别名: β,β-Trehalose
• CAS: 162678-52-6
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: HDTRYLNUVZCQOY-SOIZYFOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  189.53
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  trehalose 、 (S)-ketoprofen vinyl ester 在 吡啶 、 Bacillus licheniformis protease 作用下， 以 叔丁醇 为溶剂， 以33.2%的产率得到6-O-ketoprofen trehaloside
  参考文献：
  名称：

  Two-step enzymatic selective synthesis of water-soluble ketoprofen–saccharide conjugates in organic media

  摘要：

  Ketoprofen-saccharide conjugates were synthesized by selectively enzymatic hydrolysis and acylation. Firstly, the (S)-ketoprofen vinyl ester was prepared by enzymatic hydrolysis of (R, S)-ketoprofen vinyl ester. Then enzymatic transesterification of (S)-ketoprofen vinyl ester with a series of saccharides were performed by the catalysis of a commercial protease from Bacillus licheniformis (BLP) in organic medium mixture of pyridine and tert-butanol. The ketoprofen was selectively conjugated onto the primary hydroxyl group of saccharides and with high yield after 72 h. Partition coefficient determination showed that all the products have better water solubility than parent ketoprofen. Chemical hydrolysis experiment indicated that 50% ketoprofen could be release from ketoprofen glucoside and maltoside in aqueous buffer (pH 7.4) within 48 h. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.040
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 、 2,3,4,6-tetra-O-benzoyl-L-glucose 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 溶剂黄146 作用下， 生成 trehalose 、 trehalose 、 trehalose
  参考文献：
  名称：

  The use of O-glycosyl trichloroacetimidates in the synthesis of unsymmetrical trehalose analogues

  摘要：

  The coupling of O-glycosyltrichloroacetimidates with 2,3,4,6-tetra-O-benzylated monosaccharides (gluco, manno, galacto) promoted by TMSOTf is described, and the compositions of the crude reaction mixtures, determined by C-13 NMR spectroscopy, are presented. Unsymmetrical trehalose derivatives can be synthesized by such couplings. The versatility of the trichloroacetimidates for the synthesis of trehalose analogues has furthermore been demonstrated by the glycosylation of anomerically unprotected maltose heptabenzoylate affording two trehalose-containing trisaccharides, and by the synthesis of alpha-D-galactopyranosyl alpha-D-mannopyranoside.

  DOI：

  10.1016/s0957-4166(00)86287-4