benzyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose | 115193-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose
• CAS: 115193-05-0
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: XFVFFKSIQUEEKF-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 N-溴代丁二酰亚胺(NBS) 、 IR-120(H⁺) 、 碳酸氢钠 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium bromide 、 silver(l) oxide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.08h， 生成 (2R,4R,5R,6R)-4,5,6-Tris-benzyloxy-3-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of β-d-Gluco-, α-l-Ido-, and α-l-Altropyranosiduronic Acids from Δ⁴-Uronates

  摘要：

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

  DOI：

  10.1021/jo981477k
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 氢溴酸 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 silver carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.25h， 生成 benzyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of β-d-Gluco-, α-l-Ido-, and α-l-Altropyranosiduronic Acids from Δ⁴-Uronates

  摘要：

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

  DOI：

  10.1021/jo981477k

文献信息

• Synthesis of monosaccharide-fused azetidines
  作者：Thierry Michaud、Josette Chanet-Ray、Sithan Chou、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00015-3

  日期：1997.4

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.