D-ery-a-L-manNon2ulo3Br5NAc-onic | 374726-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-ery-a-L-manNon2ulo3Br5NAc-onic
• 英文别名: (2R,3R,4R,5R,6R)-5-acetamido-3-bromo-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 374726-23-5
• 化学式: C₁₁H₁₈BrNO₉
• 分子量: 388.169
• InChiKey: OIAZFGBXAUACMI-RISWTRDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 D-ery-a-L-manNon2ulo3Br5NAc-onic 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 (2S,3R,4R,5S,6R)-2,4-Diacetoxy-5-acetylamino-3-bromo-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Chloroperoxidase-catalyzed asymmetric synthesis: enantioselective reactions of chiral hydroperoxides with sulfides and bromohydroxylation of glycals

  摘要：

  This paper describes the use of chloroperoxidase (CPO) from Caldanomyces fumago in the oxidation of sulfides to prepare (R)-sulfoxides with excellent ee (97-100%) and yield (66-92%) using H2O2 as oxidant. When racemic 1-phenylethyl hydroperoxides were used in the oxidation of sulfides, the corresponding (R)-alcohol generated from the oxidant and the unreacted (S)-hydroperoxide were recovered with high enantiomeric purity. The enantioselectivity in the enzymatic asymmetric oxidation was found to depend on the concentrations of the substrate and enzyme. Chloroperoxidase was also used in the regioselective bromohydration of certain saccharide glycals with KBr and H2O2 to give the corresponding 2-deoxy-2-bromo saccharides.

  DOI：

  10.1021/jo00052a048
• 作为产物：
  描述：

  N-乙酰-2,3-二脱氢-2-脱氧神经氨酸 在 chloroperoxydase 双氧水 、 potassium bromide 作用下， 生成 D-ery-a-L-manNon2ulo3Br5NAc-onic
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.

  DOI：

  10.1021/jo00083a032

文献信息

• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
• Chloroperoxidase-catalyzed asymmetric synthesis: enantioselective reactions of chiral hydroperoxides with sulfides and bromohydroxylation of glycals
  作者：Hong Fu、Hirosato Kondo、Yoshitaka Ichikawa、Gary C. Look、Chi Huey Wong

  DOI：10.1021/jo00052a048

  日期：1992.12

  This paper describes the use of chloroperoxidase (CPO) from Caldanomyces fumago in the oxidation of sulfides to prepare (R)-sulfoxides with excellent ee (97-100%) and yield (66-92%) using H2O2 as oxidant. When racemic 1-phenylethyl hydroperoxides were used in the oxidation of sulfides, the corresponding (R)-alcohol generated from the oxidant and the unreacted (S)-hydroperoxide were recovered with high enantiomeric purity. The enantioselectivity in the enzymatic asymmetric oxidation was found to depend on the concentrations of the substrate and enzyme. Chloroperoxidase was also used in the regioselective bromohydration of certain saccharide glycals with KBr and H2O2 to give the corresponding 2-deoxy-2-bromo saccharides.