3-O-acetyl-β-D-arabinofuranose 1,2,5-orthobenzoate | 1263058-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3-O-acetyl-β-D-arabinofuranose 1,2,5-orthobenzoate
• CAS: 1263058-09-8
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: QGORIDRSTSKHSD-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-β-D-arabinofuranose 1,2,5-orthobenzoate 、 乙硫醇 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到ethyl 3-O-acetyl-2-O-benzoyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks

  摘要：

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.002
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 1,1-二氯甲醚 、 四丁基溴化铵 、 sodium methylate 、 四氯化锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 3-O-acetyl-β-D-arabinofuranose 1,2,5-orthobenzoate
  参考文献：
  名称：

  Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks

  摘要：

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.002