para-nitrophenyl 2-O,5-C-methylene-β-D-glucopyranoside | 612841-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: para-nitrophenyl 2-O,5-C-methylene-β-D-glucopyranoside
• 英文别名: (1S,3R,4R,7S,8S)-1-(hydroxymethyl)-3-(4-nitrophenoxy)-2,5-dioxabicyclo[2.2.2]octane-7,8-diol
• CAS: 612841-69-7
• 化学式: C₁₃H₁₅NO₈
• 分子量: 313.264
• InChiKey: GBJJTZGFCFRKHF-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  para-nitrophenyl 2-O,5-C-methylene-β-D-glucopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.009
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 sodium bromate 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 sodium dithionite 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 臭氧 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 para-nitrophenyl 2-O,5-C-methylene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of B2,5 type conformationally constrained glucopyranosides

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides restrained in a conformation close to B-2,B-5 have been synthesized. They are all hydrolyzed at similar rates, close to those observed for the parent unlocked glucosides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01631-9

文献信息

• Synthesis of B2,5 type conformationally constrained glucopyranosides
  作者：Yves Blériot、Subramanian K Vadivel、Ian R Greig、Anthony J Kirby、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(03)01631-9

  日期：2003.8

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides restrained in a conformation close to B-2,B-5 have been synthesized. They are all hydrolyzed at similar rates, close to those observed for the parent unlocked glucosides. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue
  作者：Yves Blériot、Subramanian K. Vadivel、Antonio J. Herrera、Ian R. Greig、Anthony J. Kirby、Pierre Sinaÿ

  DOI：10.1016/j.tet.2004.06.009

  日期：2004.8

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.