methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talohexopyranoside | 218445-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talohexopyranoside
• 英文别名: methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talopyranoside；(2S,3S,4R,5R,6R)-2-methoxy-3-methyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 218445-42-2
• 化学式: C₂₉H₃₄O₅
• 分子量: 462.586
• InChiKey: RJNUFUTUKDTBEZ-MEGPWYFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talohexopyranoside 在 硫酸 、 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 以48%的产率得到3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talohexopyranosyl 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
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-α-D-lycohexopyranoside 在 氢气 作用下， 以92%的产率得到methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-methyl-α-D-talohexopyranoside
  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

• Platinum-Catalyzed Ring Opening of 1,2-Cyclopropanated Sugars with <i>O</i>-Nucleophiles. Convenient Synthesis of 2-<i>C</i>-Branched Carbohydrates
  作者：Jürgen Beyer、Philip R. Skaanderup、Robert Madsen

  DOI：10.1021/ja001558+

  日期：2000.10.1

  in the ring opening with alcohols regardless of the stereochemistry of the starting cyclopropane. When electron-rich phenols are employed as O-nucleophiles, rearrangement to the glycosyl arene has been observed. In general, the ring opening occurs readily with unsubstituted sugar cyclopropanes to give 2-C-methyl carbohydrates. However, cyclopropanes with ester or alkyl substituents are significantly

  描述了一种由 Zeise 的二聚体催化的新反应，该反应允许 1,2-环丙烷化糖与 O-亲核试剂开环，得到 2-C-支链碳水化合物。许多 O-亲核试剂可以参与开环，包括醇类、酚类和水。已使用范围广泛的醇，产生从简单的甲基糖苷到更复杂的二糖的 2-C 支链糖苷。在新形成的 C-1 立体中心获得了非常高的非对映选择性。无论起始环丙烷的立体化学如何，α-糖苷受异头效应的青睐，始终是与醇开环的主要产物。当富电子酚用作 O-亲核试剂时，已观察到重排为糖基芳烃。一般来说，未取代的糖环丙烷很容易开环，得到 2-C-甲基碳水化合物。然而，带有酯或烷基取代基的环丙烷反应性明显较低，有些甚至完全在...
• Novel Platinum-Catalyzed Ring-Opening of 1,2-Cyclopropanated Sugars with Alcohols. Stereoselective Synthesis of 2-C-Branched Glycosides
  作者：Jürgen Beyer、Robert Madsen

  DOI：10.1021/ja982964k

  日期：1998.11.1
• 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.