methyl 2,3-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-α-D-glucopyranoside | 1616283-64-7

• 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-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-α-D-glucopyranoside
• 英文别名: 2-deoxy-D-lyxHex3Ac4Ac6Ac(b1-6)[Bn(-2)][Bn(-3)]a-Glc1Me；[(2R,3R,4R,6R)-3,4-diacetyloxy-6-[[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1616283-64-7
• 化学式: C₃₃H₄₂O₁₃
• 分子量: 646.689
• InChiKey: QQAXONYHRTYXHP-SGSVQRLMSA-N

物化性质

• 沸点：
  726.7±60.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-lyxo-hexopyranose 在 二苯基酸 、 三氯化硼 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 methyl 2,3-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-α-D-glucopyranoside 、 methyl 2,3-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages

  摘要：

  A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

  DOI：

  10.1021/ol501711v