6-O-azido-6-deoxy-1,2-O-isopropylidene-3-O-methyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose | 511269-82-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6-O-azido-6-deoxy-1,2-O-isopropylidene-3-O-methyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose
• 英文别名: [(1R)-1-[(3aR,5S,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-azidoethyl] trifluoromethanesulfonate
• CAS: 511269-82-2
• 化学式: C₁₁H₁₆F₃N₃O₇S
• 分子量: 391.325
• InChiKey: MSSGPNQECQTKNB-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-O-azido-6-deoxy-1,2-O-isopropylidene-3-O-methyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose 在 镍 sodium azide 、 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.58h， 生成 5,6-di-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose
  参考文献：
  名称：

  Mild and efficient synthesis of 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-l-idofuranose: precursor of the first carbohydrate-derived chiral Mn(III)–salen complex

  摘要：

  Carbohydrates as multifunctional naturally occurred chiral products were used for the first time as chiral building blocks in Mn(III)-salen complexes as catalysts for the enantioselective epoxidation of alkenes. The pathways of the mild and efficient synthesis of a Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-beta-L-idofuranose starting from D-(+)-glucose are described. The complex efficiently catalyzed the epoxidation of styrene and 1,2-dihydronaphthalene, using aqueous sodium hypochlorite in CH2Cl2 as terminal oxidant. The enantiomeric excesses were 13 and 33%, respectively. Mn(III)-salen catalyst with only one stereogenic carbon atom that is adjacent to nitrogen atom proved to be able to show enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01294-2
• 作为产物：
  描述：

  双丙酮葡萄糖 在 吡啶 、 氢氧化钾 、 sodium azide 、 四丁基溴化铵 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.33h， 生成 6-O-azido-6-deoxy-1,2-O-isopropylidene-3-O-methyl-5-O-trifluoromethanesulfonyl-α-D-glucofuranose
  参考文献：
  名称：

  Mild and efficient synthesis of 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-l-idofuranose: precursor of the first carbohydrate-derived chiral Mn(III)–salen complex

  摘要：

  Carbohydrates as multifunctional naturally occurred chiral products were used for the first time as chiral building blocks in Mn(III)-salen complexes as catalysts for the enantioselective epoxidation of alkenes. The pathways of the mild and efficient synthesis of a Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-beta-L-idofuranose starting from D-(+)-glucose are described. The complex efficiently catalyzed the epoxidation of styrene and 1,2-dihydronaphthalene, using aqueous sodium hypochlorite in CH2Cl2 as terminal oxidant. The enantiomeric excesses were 13 and 33%, respectively. Mn(III)-salen catalyst with only one stereogenic carbon atom that is adjacent to nitrogen atom proved to be able to show enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01294-2

文献信息

• Mild and efficient synthesis of 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-l-idofuranose: precursor of the first carbohydrate-derived chiral Mn(III)–salen complex
  作者：Shanhong Yan、Dieter Klemm

  DOI：10.1016/s0040-4020(02)01294-2

  日期：2002.12

  Carbohydrates as multifunctional naturally occurred chiral products were used for the first time as chiral building blocks in Mn(III)-salen complexes as catalysts for the enantioselective epoxidation of alkenes. The pathways of the mild and efficient synthesis of a Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-beta-L-idofuranose starting from D-(+)-glucose are described. The complex efficiently catalyzed the epoxidation of styrene and 1,2-dihydronaphthalene, using aqueous sodium hypochlorite in CH2Cl2 as terminal oxidant. The enantiomeric excesses were 13 and 33%, respectively. Mn(III)-salen catalyst with only one stereogenic carbon atom that is adjacent to nitrogen atom proved to be able to show enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.