methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-hydroxy-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-arabino-hex-5-enopyranoside | 824410-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-hydroxy-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-arabino-hex-5-enopyranoside
• CAS: 824410-30-2
• 化学式: C₄₆H₅₂O₁₂
• 分子量: 796.912
• InChiKey: DSKAYYKUEMOXPS-NURVDNCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  137.44
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-hydroxy-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-arabino-hex-5-enopyranoside 在 吡啶 、 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 30.5h， 生成 1,2,3-tri-O-acetyl-4-C-acetyl-(S)-5-C-[2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl]-4-deoxy-β-L-arabinopyranose
  参考文献：
  名称：

  Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1→4)-C-disaccharides

  摘要：

  Starting from methyl 6-bromo-4,6-dideoxy-alpha-D-threo-4-enopyranoside, 4-C-branched sugars have been prepared through indium-promoted Barbier-type allylation of various aldehydes in aqueous media followed by hydroboration of the resulting double bond. The intermediate unsaturated monosaccharides were shown to rearrange in acidic media to give 4-C-acetyl-5-C-alkyl pyranose compounds. From beta-1-formyl sugars the corresponding beta-(1-->4)-C-disaccharides were obtained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.09.010
• 作为产物：
  描述：

  methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside 在 吡啶 、 indium 、 phosphate buffer 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-hydroxy-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-arabino-hex-5-enopyranoside
  参考文献：
  名称：

  Indium-promoted Barbier-type allylations in aqueous media: a convenient approach to 4-C-branched monosaccharides and (1→4)-C-disaccharides

  摘要：

  Starting from methyl 6-bromo-4,6-dideoxy-alpha-D-threo-4-enopyranoside, 4-C-branched sugars have been prepared through indium-promoted Barbier-type allylation of various aldehydes in aqueous media followed by hydroboration of the resulting double bond. The intermediate unsaturated monosaccharides were shown to rearrange in acidic media to give 4-C-acetyl-5-C-alkyl pyranose compounds. From beta-1-formyl sugars the corresponding beta-(1-->4)-C-disaccharides were obtained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.09.010