β-D-arabinofuranose 1,2,5-orthobenzoate | 282107-49-7

• 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: β-D-arabinofuranose 1,2,5-orthobenzoate
• 英文别名: (1R,3S,5S,7S,8R)-5-phenyl-2,4,6,10-tetraoxatricyclo[3.3.2.03,7]decan-8-ol
• CAS: 282107-49-7
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: XJXQECGESXBZKT-GCHJQGSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-D-arabinofuranose 1,2,5-orthobenzoate 在 吡啶 、 咪唑 、 4 A molecular sieve 、 sodium methylate 、 四氯化锡 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(9-fluorenylmethoxycarbonyl)-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Elaboration of Monoarabinofuranosidic Building Blocks

  摘要：

  DOI：

  10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 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 16.0h， 生成 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

文献信息

• Cyclization of β-d-arabinofuranose 1,2-methyl)orthobenzoate using magnesium bromide
  作者：N. M. Podvalnyy、A. I. Zinin、P. I. Abronina、V. I. Torgov、L. O. Kononov

  DOI：10.1007/s11172-010-0038-y

  日期：2009.2

  Transformation of β-d-arabinofuranose 1,2-(methyl)orthobenzoate into β-d-arabinofuranose 1,2,5-orthobenzoate has been accomplished upon heating with magnesium bromide in THF. The new cyclization conditions can be applied for preparing the tricyclic 1,2,5-orthobenzoate on a gram scale.

  在四氢呋喃溶液中加热溴化镁后，β-d-阿拉伯呋喃糖 1,2-（甲基）原苯甲酸酯转化为 β-d-阿拉伯呋喃糖 1,2,5-正苯甲酸酯。新的环化条件可用于制备克级的三环 1,2,5-正苯甲酸酯。
• Elaboration of Monoarabinofuranosidic Building Blocks
  作者：Sylvie Sanchez、Toufiq Bamhaoud、Jacques Prandi

  DOI：10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8

  日期：2002.11
• Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
  作者：Nikita M. Podvalnyy、Sergey L. Sedinkin、Polina I. Abronina、Alexander I. Zinin、Ksenia G. Fedina、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2010.11.002

  日期：2011.1

  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.