(2S,3R,4S,5R)-5-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-methoxy-6-methylene-tetrahydro-pyran-3,4-diol | 824410-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,4S,5R)-5-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-methoxy-6-methylene-tetrahydro-pyran-3,4-diol
• CAS: 824410-17-5
• 化学式: C₂₂H₃₀O₉
• 分子量: 438.475
• InChiKey: ASUUKMLJSOVBFV-UJGXVNFHSA-N

物化性质

• 沸点：
  580.8±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  116.07
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-5-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-methoxy-6-methylene-tetrahydro-pyran-3,4-diol 在 吡啶 、 盐酸 作用下， 反应 0.5h， 生成 1,2,3-tri-O-acetyl-4-C-acetyl-5-(S)-C-[3'-O-benzyl-1',2'-di-O-isopropylidene-4'-(S)-C-α-D-threofuranosyl]-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：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 、 methyl 6-bromo-4,6-dideoxy-α-D-threo-hex-4-enopyranoside 在 indium 、 phosphate buffer 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以57%的产率得到(2S,3R,4S,5R)-5-[(S)-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hydroxy-methyl]-2-methoxy-6-methylene-tetrahydro-pyran-3,4-diol
  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