3,5-di-O-benzyl-2-deoxy-β-D-erythropentofuranosyl hydroperoxide | 861100-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-benzyl-2-deoxy-β-D-erythropentofuranosyl hydroperoxide
• 英文别名: (2R,3S,5S)-5-hydroperoxy-3-phenylmethoxy-2-(phenylmethoxymethyl)oxolane
• CAS: 861100-51-8
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: LUVWRAMLFSBICJ-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  3,5-di-O-benzyl-2-deoxy-β-D-erythropentofuranosyl hydroperoxide 、 methyl 3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranoside 在 (+)-10-camphorsulfonic acid 作用下， 以 二氯甲烷 为溶剂， 生成 3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl(3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl)peroxide
  参考文献：
  名称：

  Bisglycosyl Peroxides

  摘要：

  三O-苄基-d-甘露糖在per-O-苄基-2-脱氧-α-或per-O-苄基-2-脱氧-β-d-糖苷过氧化物的处理下，生成相应的双糖苷过氧化物。在所有情况下，形成了新的α-糖苷键。过氧化物的形成不是一个可逆的过程；在所施加的反应条件下，我们没有观察到β,α-过氧化物转变为相应的α,α-化合物。

  DOI：

  10.1055/s-2007-991090
• 作为产物：
  描述：

  methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside 在 硫酸 、 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 以42%的产率得到3,5-di-O-benzyl-2-deoxy-α-D-erythropentofuranosyl hydroperoxide
  参考文献：
  名称：

  New stable anomeric hydroperoxides derived from 2-deoxysugars; enantioselective epoxidation of 2-methyl-1,4-naphthoquinone

  摘要：

  3.5-Di- or 3,4,6-tri-O-substituted-2-deoxysugars or their glycosides can be oxidized with hydrogen peroxide in the presence of an acid catalyst to the corresponding anomeric hydroperoxides, which are relatively stable, can be separated into pure anomers by column chromatography and stored in a refrigerator without visible decomposition. The hydroperoxides thus obtained were used for the enantioselective epoxidation of 2-methyl-1,4-naphthoquinone with ees in the range 28-47%. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.009

文献信息

• Bisglycosyl Peroxides
  作者：Marek Chmielewski、Wioletta Kośnik、Barbara Grzeszczyk

  DOI：10.1055/s-2007-991090

  日期：——

  Tri-O-benzyl-d-glycal treated with per-O-benzyl-2-deoxy-α- or per-O-benzyl-2-deoxy-β-d-glycosyl hydroperoxide affords the corresponding bisglycosyl peroxides. In all cases a new α-glycosidic bond is formed. Formation of the peroxide is not a reversible process; under applied reaction conditions, we did not observe rearrangement of β,α-peroxide into the corresponding α,α-compounds.

  三O-苄基-d-甘露糖在per-O-苄基-2-脱氧-α-或per-O-苄基-2-脱氧-β-d-糖苷过氧化物的处理下，生成相应的双糖苷过氧化物。在所有情况下，形成了新的α-糖苷键。过氧化物的形成不是一个可逆的过程；在所施加的反应条件下，我们没有观察到β,α-过氧化物转变为相应的α,α-化合物。
• New stable anomeric hydroperoxides derived from 2-deoxysugars; enantioselective epoxidation of 2-methyl-1,4-naphthoquinone
  作者：Wioletta Kośnik、Andrew V. Stachulski、Marek Chmielewski

  DOI：10.1016/j.tetasy.2005.04.009

  日期：2005.6

  3.5-Di- or 3,4,6-tri-O-substituted-2-deoxysugars or their glycosides can be oxidized with hydrogen peroxide in the presence of an acid catalyst to the corresponding anomeric hydroperoxides, which are relatively stable, can be separated into pure anomers by column chromatography and stored in a refrigerator without visible decomposition. The hydroperoxides thus obtained were used for the enantioselective epoxidation of 2-methyl-1,4-naphthoquinone with ees in the range 28-47%. (c) 2005 Elsevier Ltd. All rights reserved.