1,5-anhydro-2,3-O-isopropylidene-β-D-tagatopyranose | 871507-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3-O-isopropylidene-β-D-tagatopyranose
• 英文别名: (1S,5S,6S,7R)-3,3-dimethyl-2,4,8,10-tetraoxatricyclo[5.2.2.01,5]undecan-6-ol
• CAS: 871507-99-2
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: GMJISJZEUCYDHR-XKBZYTNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3-O-isopropylidene-β-D-tagatopyranose 、 2,3,4,6-四-O-乙酰基-Alpha-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到1,5-anhydro-2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-tagatopyranose
  参考文献：
  名称：

  Synthesis of 4-O-glycosylated 1,5-anhydro-d-fructose and of 1,5-anhydro-d-tagatose from a common intermediate 2,3-O-isopropylidene-d-fructose

  摘要：

  Four novel disaccharides of glycosylated 1,5-anhydro-D-ketoses have been prepared: 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-tagatose, and 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-beta-D-fructopyranose, was prepared from D-fructose and was converted into the D-tagatose derivative by oxidation followed by stereoselective reduction to the 4-epimer. The anhydroketoses thus prepared were glycosylated and deprotected to give the disaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.005
• 作为产物：
  描述：

  1,5-anhydro-2,3-O-isopropylidene-D-threo-hex-4-ulopyran-2-ose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到1,5-anhydro-2,3-O-isopropylidene-β-D-tagatopyranose
  参考文献：
  名称：

  Synthesis of 4-O-glycosylated 1,5-anhydro-d-fructose and of 1,5-anhydro-d-tagatose from a common intermediate 2,3-O-isopropylidene-d-fructose

  摘要：

  Four novel disaccharides of glycosylated 1,5-anhydro-D-ketoses have been prepared: 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-tagatose, and 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-beta-D-fructopyranose, was prepared from D-fructose and was converted into the D-tagatose derivative by oxidation followed by stereoselective reduction to the 4-epimer. The anhydroketoses thus prepared were glycosylated and deprotected to give the disaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.005