α-D-glucose-5,6,6-d3 | 6763-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucose-5,6,6-d3
• 英文别名: (2S,3R,4S,5S,6R)-6-deuterio-6-[dideuterio(hydroxy)methyl]oxane-2,3,4,5-tetrol
• CAS: 6763-33-3
• 化学式: C₆H₁₂O₆
• 分子量: 183.134
• InChiKey: WQZGKKKJIJFFOK-UHOZHJTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.22
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1,2-O-isopropylidene-α-D-5,6,6'-(²H₃)-glucofuranose 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 5,6,6-2H3-β-D-glucopyranose 、 α-D-glucose-5,6,6-d3
  参考文献：
  名称：

  Regioselective synthesis of 1I,1II,5I,5II,6I,6I,6II,6II-2H8-cellobiose

  摘要：

  Partially deuteriated 1,5,6,6-H-2(4)-D-glucose and (I),1(II),5(I),5(II),6(I),6(II),6(II)-H-2(8)-cellobiose were synthesized in high yields and on a large scale from D-glucose. (2) H enrichment at C-5 and C-6 of each glucopyranosyl unit in excess of 85% and 90%, respectively, was realized by H-1-H-2 exchange in (H2O)-H-2 containing deuteriated Raney Ni. Nucleophilic addition of LiAlD4 to 5,6,6-H-2(3)-2,3,4,6-tetra-O-benzyl-D-gluconolactone led to a 98% H-2 enrichment at C-1. Deuteriated cellobiose is of interest as building block for the synthesis of a model compound of cellulose I. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.07.017