[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-methylbut-2-enoxy)oxan-2-yl]methyl acetate | 212763-60-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-methylbut-2-enoxy)oxan-2-yl]methyl acetate
• CAS: 212763-60-5
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: IQQWIUSWDDGXFO-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-methylbut-2-enoxy)oxan-2-yl]methyl acetate 在 二甲基硫 、 臭氧 作用下， 生成 2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyl)ethanal
  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 、 β-glucosidase 作用下， 反应 24.25h， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-methylbut-2-enoxy)oxan-2-yl]methyl acetate
  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

文献信息

• Chemoenzymatic syntheses of naturally occurring β-glucosides
  作者：Hiroyuki Akita、Katsumi Kurashima、Takuya Nakamura、Keisuke Kato

  DOI：10.1016/s0957-4166(99)00228-1

  日期：1999.6

  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.