p-nitrophenyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside | 221697-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-(4-nitrophenoxy)-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 221697-42-3
• 化学式: C₃₃H₃₃NO₈
• 分子量: 571.627
• InChiKey: WQXRLSZWTXTQJE-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 palladium dihydroxide 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 p-methacryloylamidophenyl 2,3,4-tri-O-benzyl-6-O-phosphorylcholine-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Artificial Glycoconjugate Polymers Carrying 6-O-Phosphocholine α-D-Glucopyranoside, Biologically Active Segment of Main Cell Membrane Glycolipids ofMycoplasma Fermentas

  摘要：

  As carbohydrate probes to investigate the biological activity of novel phosphocholine-containing glycoglycerolipids of M. fermentans, artificial glycoconjugate polymers carrying 6-O-phosphocholine alpha-D-glucopyranoside were synthesized. The synthesis involved a-selective 1-O-p-nitrophenylation (pNP) of 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose in the presence of a Lewis acid followed by the introduction of a phosphocholine group at position O-6 by an amidite method. The pNP group was converted into ap -N-methacrylamidophenyl group for subsequent radical polymerization.

  DOI：

  10.1080/07328309908544048
• 作为产物：
  描述：

  p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 p-nitrophenyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 p-nitrophenyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Artificial Glycoconjugate Polymers Carrying 6-O-Phosphocholine α-D-Glucopyranoside, Biologically Active Segment of Main Cell Membrane Glycolipids ofMycoplasma Fermentas

  摘要：

  As carbohydrate probes to investigate the biological activity of novel phosphocholine-containing glycoglycerolipids of M. fermentans, artificial glycoconjugate polymers carrying 6-O-phosphocholine alpha-D-glucopyranoside were synthesized. The synthesis involved a-selective 1-O-p-nitrophenylation (pNP) of 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose in the presence of a Lewis acid followed by the introduction of a phosphocholine group at position O-6 by an amidite method. The pNP group was converted into ap -N-methacrylamidophenyl group for subsequent radical polymerization.

  DOI：

  10.1080/07328309908544048

文献信息

• Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans
  作者：Yoshihiro Nishida、Yusuke Takamori、Hiroshi Ohrui、Ineo Ishizuka、Kazuhiro Matsuda、Kazukiyo Kobayashi

  DOI：10.1016/s0040-4039(99)00191-4

  日期：1999.3

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.