methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside | 824410-29-9

• 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-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside
• 英文别名: [(2S,3R,4S,5S)-3-acetyloxy-5-[(S)-acetyloxy-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-2-methoxy-6-methylideneoxan-4-yl] acetate
• CAS: 824410-29-9
• 化学式: C₄₈H₅₄O₁₃
• 分子量: 838.949
• InChiKey: PAYPNYBZWFVDJJ-OGEZUCTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-acetyl-4-C-[(S)-1-O-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-hex-5-enopyranoside 在 硼烷四氢呋喃络合物 、 phosphate buffer 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Acetic acid (S)-((2R,3S,4S,5R,6S)-4,5-diacetoxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methyl ester
  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-acetyl-1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-methyl]-4,6-dideoxy-α-D-xylo-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