methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside | 824410-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside
• 英文别名: (2S,3R,4S)-6-(bromomethyl)-2-methoxy-3,4-dihydro-2H-pyran-3,4-diol
• CAS: 824410-14-2
• 化学式: C₇H₁₁BrO₄
• 分子量: 239.066
• InChiKey: OTYMWRUVDKNUFU-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside 在 盐酸 、 indium 、 phosphate buffer 作用下， 以 四氢呋喃 为溶剂， 反应 1.58h， 生成 4-C-acetyl-5-(S)-C-phenyl-4-deoxy-α-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 2,3-di-O-acetyl-6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 以97%的产率得到methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-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