1-O-phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranose | 22348-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranose
• 英文别名: phenyl-(O²,O³,O⁴-triacetyl-β-D-glucopyranoside)；Phenyl-(O²,O³,O⁴-triacetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(hydroxymethyl)-6-phenoxyoxan-3-yl] acetate
• CAS: 22348-21-6
• 化学式: C₁₈H₂₂O₉
• 分子量: 382.367
• InChiKey: ZWTDJFRCKBKITF-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranose 在 吡啶 、 氢氧化钾 作用下， 生成 phenyl-[O²,O³,O⁶-triacetyl-O⁴-(toluene-4-sulfonyl)-β-D-glucopyranoside]
  参考文献：
  名称：

  Helferich; Strauss, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 142, p. 13,17

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 吡啶 、 碘 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1-O-phenyl-2,3,4-tri-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  A novel synthetic strategy for monosubstituted cyclodextrin derivatives

  摘要：

  已经开发了一种首次固相法，以获取与不同标签的单取代环糊精（CD）共轭物。设计了一种新的固相支撑，能够通过磷酸二酯桥与不同标签共价连接，获得多种C-6单功能化的环糊精（α、β、MeβCD和HPβCD），并且在非常温和的脱离条件下以高纯度形式存在。

  DOI：

  10.1039/c2cc30550j

文献信息

• Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases
  作者：Adriano A. Mendes、Dasciana S. Rodrigues、Marco Filice、Roberto Fernandez-Lafuente、Jose M. Guisan、Jose M. Palomo

  DOI：10.1016/j.tet.2008.08.099

  日期：2008.11

  The regioselective monohydrolysis of different peracetylated-beta-glucopyranosides in aqueous media using immobilized preparations of three different lipases-those from Aspergillus niger (ANL), Candida rugose (CRL) and Candida antarctica B (CAL-B)-has been Studied. Three very different immobilization strategies-covalent attachment, anionic exchange and interfacial activation oil a hydrophobic sopport-were employed for each lipase. The role of the immobilization strategy and the effect of the presence of different moieties in the anomeric position of the substrate on the hydrolytic activities, specificities and regioselectivities of the lipases were investigated. For example, the PEI-ANL preparation exhibited 800 times higher activity than the octyl-ANL in the hydrolysis of 2-acetamido-2-deoxy-1-(4-nitrophenyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranoside-producing 4-OH derivative in 18% yield-whereas the octyl-ANL was five times more active than the PEI-ANL in the hydrolysis of 1-(4-nitrophenyl)-2,3,4-tri-O-acetyl-beta-D-xylopyranoside, producing 4-OH monohydroxy product in >99% yield.The octyl-CRL preparation hydrolyzed regioselectively 3,4,6-tri-O-acetyl-glucal in position 6 in 68% yield while the PEI-CRL produced the 3-OH product in 11% yield, although with moderate specificity. The CNBr-CAL-B hydrolyzed specifically and regioselectively the glucal producing the 3-OH product in >99% yield. (C) 2008 Elsevier Ltd. All rights reserved.
• Helferich; Strauss, Journal fur praktische Chemie (Leipzig 1954), 1935, vol. <2> 142, p. 1316
  作者：Helferich、Strauss

  DOI：——

  日期：——