(RS)-1-phenylbutyl β-D-glucopyranoside | 1253122-34-7

• 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: (RS)-1-phenylbutyl β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1-phenylbutoxy)oxane-3,4,5-triol
• CAS: 1253122-34-7
• 化学式: C₁₆H₂₄O₆
• 分子量: 312.363
• InChiKey: JOEQOKWVOVBBHU-DJCOPSFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲基[羟基-(3,4,5-三羟基四氢吡喃-2-基)氧基磷酰]磷酸氢酯 、 (RS)-1-phenylbutyl β-D-glucopyranoside 在 plant xylosyltransferase from Catharanthus roseus 作用下， 反应 61.0h， 以21%的产率得到(R)-1-phenylbutyl β-primeveroside
  参考文献：
  名称：

  Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase

  摘要：

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.023

文献信息

• Enzymatic resolution of (RS)-1-phenylalkyl β-d-glucosides to (R)-1-phenylalkyl β-primeverosides and (S)-1-phenylalkyl β-d-glucosides via plant xylosyltransferase
  作者：Kei Shimoda、Hisashi Katsuragi

  DOI：10.1016/j.tetasy.2010.07.023

  日期：2010.8

  The stereoselective xylosylation of (RS)-1-phenylalkyl beta-D-glucosides was investigated using plant xylosyltransferase isolated from cultured Catharanthus roseus cells. Enzymatic xylosylation of (RS)-1-phenylethyl beta-D-glucoside afforded (R)-1-phenylethyl beta-primeveroside and (S)-1-phenylethyl beta-D-glucoside. The (R)-selective xylosylation of (RS)-1-phenylbutyl beta-D-glucoside also occurred to give (R)-1-phenylbutyl p-primeveroside and recovered (S)-1-phenylbutyl beta-D-glucoside. (C) 2010 Elsevier Ltd. All rights reserved.