methyl 4-O-(3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranos-2-ulosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 562075-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranos-2-ulosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,6S)-3,4-dibenzoyloxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-oxooxan-2-yl]methyl benzoate
• CAS: 562075-71-2
• 化学式: C₅₅H₅₂O₁₄
• 分子量: 937.009
• InChiKey: QXDOZJOVTKDNDI-JNOTWHJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  69
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranos-2-ulosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以710 mg的产率得到methyl 4-O-(3,4,6-tri-O-benzoyl-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  manno- versus gluco-Selectivity in reductions of 2-keto-β-d-arabino-hexopyranosides

  摘要：

  Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-beta-D-arabino-hexopyranosides to beta-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric beta-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either beta-D-Man or beta-D-Glc units. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00028-4
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide 在 4 A molecular sieve 、 silver alumosilicate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以77%的产率得到methyl 4-O-(3,4,6-tri-O-benzoyl-β-D-arabino-hexopyranos-2-ulosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  manno- versus gluco-Selectivity in reductions of 2-keto-β-d-arabino-hexopyranosides

  摘要：

  Tri-sec-butylborohydrides (L- or K-Selectride) reduce the carbonyl group in acylated 2-keto-beta-D-arabino-hexopyranosides to beta-D-mannosides in an essentially stereospecific fashion, whereas borane reduction gives the 2-epimeric beta-D-glucosides with high preference. As preparative yields are in the 70-85% range, the ulosyl donor approach can thus be utilized for the straightforward construction of oligosaccharides containing either beta-D-Man or beta-D-Glc units. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00028-4