phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-β-D-glucopyranoside | 1228930-02-6

• 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: phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-β-D-glucopyranoside
• 英文别名: phenyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-seleno-β-D-glucopyranoside；[(2R,3R,4R,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-2-(phenylmethoxymethyl)-6-phenylselanyloxan-3-yl] acetate
• CAS: 1228930-02-6
• 化学式: C₂₇H₃₈O₆SeSi
• 分子量: 565.641
• InChiKey: ZRFMVWIYPDFRJX-SDVOOXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙氧基甲基氯 、 phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-β-D-glucopyranoside 在 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 18.0h， 以73%的产率得到phenyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-2-O-(2-methoxyethoxymethyl)-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools

  摘要：

  The glycosylation of alcohols by the new 2-O-MEM-substituted D-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-beta-D-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-beta-O-glycosides, 3-deoxy-beta-D-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-beta-D-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.061
• 作为产物：
  描述：

  [(1S,3R,4R,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-3-(phenylmethoxymethyl)-2,7-dioxabicyclo[4.1.0]heptan-4-yl] acetate 、 苯硒酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以0.845 g的产率得到phenyl 4-O-acetyl-6-O-benzyl-3-O-(tert-butyldimethylsilyl)-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of 2-O-MEM-2,3-unsaturated-β-O-glycosides and elaboration to useful synthetic tools

  摘要：

  The glycosylation of alcohols by the new 2-O-MEM-substituted D-galactal-derived allyl epoxide affords the corresponding alkyl 2-O-MEM-3-deoxy-beta-D-threo-hex-2-enopyranosides through a completely 1,4-regio- and a highly to completely substrate-dependent stereoselective glycosylation processes. The glycosides obtained can be regioselectively transformed into corresponding 3-deoxy-beta-O-glycosides, 3-deoxy-beta-D-threo-hexopyranosid-2-uloses, and 3,4-dideoxy-beta-D-glycero-hex-3-enopyranosid-2-uloses, which are useful synthetic tools for further transformations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.061

文献信息

• Stereoselective Synthesis of β-Phenylselenoglycosides from Glycals and Rationalization of the Selenoglycosylation Processes
  作者：Valeria Di Bussolo、Annalisa Fiasella、Federica Balzano、Gloria Uccello Barretta、Paolo Crotti

  DOI：10.1021/jo100145s

  日期：2010.6.18

  beta-Phenylselenoglycosides have been efficiently and stereoselectively synthesized by direct oxidative glycosylation of benzenselenolate (PhSe(-)) with glycals. A rationalization of the presently described beta-selectivity and the opposite alpha-selectivity reported by Danishefsky in the ring-opening of epoxy glycals with benzeneselenol (PhSeH) is proposed.