3-hydroxybenzyl β-primeveroside | 411240-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxybenzyl β-primeveroside
• 英文别名: (2R,3R,4S,5S,6R)-2-[(3-hydroxyphenyl)methoxy]-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 411240-68-1
• 化学式: C₁₈H₂₆O₁₁
• 分子量: 418.398
• InChiKey: ZVVZDPDECXNJFV-NWQIESHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  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 、 3-hydroxybenzyl β-D-glucopyranoside 在 plant xylosyltransferase from Catharanthus roseus 作用下， 反应 36.0h， 以66%的产率得到3-hydroxybenzyl 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