1-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-phenylpropan-2-ol | 250590-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-phenylpropan-2-ol
• 英文别名: 1-phenyl-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propan-2-ol
• CAS: 250590-56-8
• 化学式: C₄₃H₄₆O₆
• 分子量: 658.835
• InChiKey: OYLCNJRZHSAEBF-IZRZDMORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-phenylpropan-2-ol 在 jones reagent 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到1-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-phenylacetone
  参考文献：
  名称：

  Synthetic Approaches to C-Glucosinolates

  摘要：

  In these pages, short and efficient synthetic approaches to C-analogs of glucosinolates are described. Starting from D-glucose, C-glucotropaeolin (6) and C-glucocapparin (11) were synthesized in three steps. Preliminary enzymatic assays involving sulfatase and myrosinase have been performed. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00153-8
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-phenylpropan-2-ol
  参考文献：
  名称：

  The first synthesis of C-glucotropaeolin

  摘要：

  Starting from tetra-O-benzyl-D-glucose (2), the first synthesis of a C-analogue 7 of glucotropaeolin, the major glucosinolate of the genus Nasturtium was performed. Compound 7 constitutes a potential non-hydrolyzable inhibitor of the enzyme myrosinase. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01416-1

文献信息

• Synthetic Approaches to C-Glucosinolates
  作者：Vincent Aucagne、David Gueyrard、Arnaud Tatibouët、Alain Quinsac、Patrick Rollin

  DOI：10.1016/s0040-4020(00)00153-8

  日期：2000.4

  In these pages, short and efficient synthetic approaches to C-analogs of glucosinolates are described. Starting from D-glucose, C-glucotropaeolin (6) and C-glucocapparin (11) were synthesized in three steps. Preliminary enzymatic assays involving sulfatase and myrosinase have been performed. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
• The first synthesis of C-glucotropaeolin
  作者：V. Aucagne、D. Gueyrard、A. Tatibouët、S. Cottaz、H. Driguez、M. Lafosse、P. Rollin

  DOI：10.1016/s0040-4039(99)01416-1

  日期：1999.10

  Starting from tetra-O-benzyl-D-glucose (2), the first synthesis of a C-analogue 7 of glucotropaeolin, the major glucosinolate of the genus Nasturtium was performed. Compound 7 constitutes a potential non-hydrolyzable inhibitor of the enzyme myrosinase. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.