1,3,4,5-tetra-O-benzyl-D-sedoheptulose | 946570-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,5-tetra-O-benzyl-D-sedoheptulose
• 英文别名: (2S,3S,4R,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-2-ol
• CAS: 946570-79-2
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: LZNNPUYHAPBHKR-DWZFQDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-benzyl-D-sedoheptulose 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 乙醇 、 乙酸乙酯 为溶剂， 反应 103.0h， 生成 7-O-galloyl-β-D-sedoheptulofuranose
  参考文献：
  名称：

  Synthesis of 7-O-galloyl-d-sedoheptulose

  摘要：

  A facile synthetic approach to 7-O-galloyl-D-sedoheptulose (1), a natural product with notable immunosuppressant activity, was developed. The starting material, 2,7-anhydro-D-sedoheptulose (2), was converted in three steps into 1,3,4,5-tetra-O-benzyl-D-sedoheptulose (5), a key intermediate that allows specific functionalization at C-7 of the sedoheptulpyranose. After regioselective esterification of 5 with 3,4,5-tri-O-benzylgalloyl acid, followed by catalytic debenzylation (Pd-C), I was obtained in an overall yield of 60%. The spectroscopic data and TLC behavior of 1 were found to be identical to that of the natural product. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.015
• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzyl-2,7-di-O-acetyl-D-sedoheptulose 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以100%的产率得到1,3,4,5-tetra-O-benzyl-D-sedoheptulose
  参考文献：
  名称：

  Synthesis of 7-O-galloyl-d-sedoheptulose

  摘要：

  A facile synthetic approach to 7-O-galloyl-D-sedoheptulose (1), a natural product with notable immunosuppressant activity, was developed. The starting material, 2,7-anhydro-D-sedoheptulose (2), was converted in three steps into 1,3,4,5-tetra-O-benzyl-D-sedoheptulose (5), a key intermediate that allows specific functionalization at C-7 of the sedoheptulpyranose. After regioselective esterification of 5 with 3,4,5-tri-O-benzylgalloyl acid, followed by catalytic debenzylation (Pd-C), I was obtained in an overall yield of 60%. The spectroscopic data and TLC behavior of 1 were found to be identical to that of the natural product. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.015