p-tolyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-thio-β-D-glucopyranoside | 1251542-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(4-methylphenyl)sulfanyl-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 1251542-36-5
• 化学式: C₂₈H₄₀O₆SSi
• 分子量: 532.774
• InChiKey: AWRQOOMBGWOMJL-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-thio-β-D-glucopyranoside 、 碘甲烷 在 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以52%的产率得到p-tolyl 2-O-methyl-4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-thio-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 、 4-甲苯硫酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以0.341 g的产率得到p-tolyl 4-O-acetyl-3-O-(t-butyldimethylsilyl)-6-O-benzyl-1-thio-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