(E)-rhodiocyanoside A tetraacetate | 245743-03-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-rhodiocyanoside A tetraacetate
• CAS: 245743-03-7
• 化学式: C₁₉H₂₅NO₁₀
• 分子量: 427.408
• InChiKey: OEYKBXRJBKEGCC-QAAFWDSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  147.45
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (E)-rhodiocyanoside A tetraacetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以87%的产率得到(E)-2-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile
  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：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 吡啶 、 4-二甲氨基吡啶 、 phosphate buffer 、 二甲基硫 、 sodium hydride 、 臭氧 、 β-glucosidase 作用下， 反应 27.5h， 生成 (E)-rhodiocyanoside A tetraacetate
  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