4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl orthoacetate) | 1344087-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl orthoacetate)
• 英文别名: (1R,3R,5S,7R,8S,9S,11R)-5-methoxy-5-methyl-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-ol
• CAS: 1344087-17-7
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: OFHNPDAZDLIDLN-PKDUHMPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-α-D-glucopyranose 1,2-O-(methyl orthoacetate) 在 咪唑 、 盐酸 、 水 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1-O-acetyl-3-O-tert-butyldimethylsilyl-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-acetyl-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 orthoacetate)
  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

文献信息

• Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy
  作者：Guangfa Wang、Zhichao Lu、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.08.008

  日期：2011.11

  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.