dimethyl (2R,4R,5R,6S)-5-hydroxy-2-methoxy-4-phenylmethoxyoxane-2,6-dicarboxylate | 186831-58-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl (2R,4R,5R,6S)-5-hydroxy-2-methoxy-4-phenylmethoxyoxane-2,6-dicarboxylate
• CAS: 186831-58-3
• 化学式: C₁₇H₂₂O₈
• 分子量: 354.357
• InChiKey: YDSZMTBKALKIOC-VWPFQQQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,4R,5R,6S)-5-hydroxy-2-methoxy-4-phenylmethoxyoxane-2,6-dicarboxylate 在 palladium on activated charcoal molecular sives 3 Angstroem 、 氢气 、 氰化汞 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue

  摘要：

  The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10073-8
• 作为产物：
  描述：

  methyl (2R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxane-2-carboxylate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 三甲基氯硅烷 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 potassium bromide 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 dimethyl (2R,4R,5R,6S)-5-hydroxy-2-methoxy-4-phenylmethoxyoxane-2,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue

  摘要：

  The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10073-8

文献信息

• Banaszek, Anna; Ciunik, Zbigniew, Tetrahedron Letters, 1997, vol. 38, # 2, p. 272 - 276
  作者：Banaszek, Anna、Ciunik, Zbigniew

  DOI：——

  日期：——
• Synthesis of the unique trisaccharide repeating unit, isolated from lipopolysaccharides Rhizobium leguminosarum bv. trifolii 24, and its analogue
  作者：Anna Banaszek

  DOI：10.1016/s0008-6215(97)10073-8

  日期：1998.1

  The synthesis of trisaccharide: 6-d-alpha-L-Talp(1-->2)-alpha-L-Rhap(1-->5)-DHA, and its analogue: 6-d-alpha-L-Talp(1-->2)-beta-L-Rhaf(1-->5)DHA is described. In the first step a disaccharide, composed of 6-d-L-Talp and L-Rhap was obtained. This, in turn, was converted to the corresponding 1-trichloroacetimidate and coupled with DHA alcohol to afford the required trisaccharide. Its analogue was achieved by the conversion of the above disaccharide to the glycosyl bromide, involving the rhamnopyranose ring scission, followed by condensation with DHA in Koenigs-Knorr procedure. (C) 1998 Elsevier Science Ltd. All rights reserved.