4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl 2-phenylorthoacetate) | 1344087-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl 2-phenylorthoacetate)
• CAS: 1344087-19-9
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: VSUUYNLRISYFAD-FGKHCZQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl 2-phenylorthoacetate) 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 3-O-acetyl-1-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranose
  参考文献：
  名称：

  Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy

  摘要：

  A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.008
• 作为产物：
  描述：

  ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.03h， 生成 4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl 2-phenylorthoacetate)
  参考文献：
  名称：

  Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy

  摘要：

  A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.008