3,5-di-O-benzoyl-α-D-xylo-furanose 1,2-thiocarbonate | 191538-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-di-O-benzoyl-α-D-xylo-furanose 1,2-thiocarbonate
• 英文别名: [(3aR,5R,6S,6aR)-6-benzoyloxy-2-sulfanylidene-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 191538-37-1
• 化学式: C₂₀H₁₆O₇S
• 分子量: 400.409
• InChiKey: RABJPECEXGCJKS-YYAJDYIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-α-D-xylo-furanose 1,2-thiocarbonate 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 12.42h， 生成 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)uracil
  参考文献：
  名称：

  Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates

  摘要：

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.037
• 作为产物：
  描述：

  硫光气 、 3,5-di-O-benzoyl-D-xylofuranose 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到3,5-di-O-benzoyl-α-D-xylo-furanose 1,2-thiocarbonate
  参考文献：
  名称：

  Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters

  摘要：

  Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-riba, D-allo configurations were used as starting material to afford the corresponding C-3,4 D-threo and D-erythro glycals derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00072-4

文献信息

• Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates
  作者：Rafael Robles、Concepción Rodrı́guez、Luis Álvarez de Cienfuegos、Antonio J. Mota

  DOI：10.1016/j.tetasy.2003.12.037

  日期：2004.3

  Cyclic 1,2-thiocarbonates of alpha-D-xylo- and alpha-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording beta-nucleosides with complete stereo selectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an S(N)2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl)acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1' were ascertained by chemical correlation synthesizing the corresponding 2,2'-anhydronucleosides. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters
  作者：Rafael Robles Diaz、Concepción Rodríguez Melgarejo、Isidoro Izquierdo Cubero、María T. Plaza López-Espinosa

  DOI：10.1016/s0008-6215(97)00072-4

  日期：1997.5

  Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-riba, D-allo configurations were used as starting material to afford the corresponding C-3,4 D-threo and D-erythro glycals derivatives. (C) 1997 Elsevier Science Ltd.