2-benzyloxy-3-hydroxy-2-propan-1-ol β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-benzyloxy-3-hydroxy-2-propan-1-ol β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(3-hydroxy-2-phenylmethoxypropoxy)oxane-3,4,5-triol
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: CDWBXXAOFJOYIG-DJCOPSFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-benzyloxy-3-hydroxy-2-propan-1-ol β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1
• 作为产物：
  描述：

  2-苄氧基-1,3-丙二醇 、 4-硝基苯-Β-D-吡喃葡萄糖苷 在 phosphate buffer 、 β-glucosidase 作用下， 反应 4.0h， 以22%的产率得到2-benzyloxy-3-hydroxy-2-propan-1-ol β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1