para-nitrophenyl 6-O-benzoyl-2-O,5-C-methylene-β-D-glucopyranoside | 612841-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: para-nitrophenyl 6-O-benzoyl-2-O,5-C-methylene-β-D-glucopyranoside
• CAS: 612841-82-4
• 化学式: C₂₀H₁₉NO₉
• 分子量: 417.372
• InChiKey: OUGATUPEVZBHTG-HPUSYDDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  137.59
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  para-nitrophenyl 6-O-benzoyl-2-O,5-C-methylene-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到para-nitrophenyl 2-O,5-C-methylene-β-D-glucopyranoside
  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：

  (2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-7-hydroxy-2-phenyl-6-phenylsulfanyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carbaldehyde 在 吡啶 、 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 、 4 A molecular sieve 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.0h， 生成 para-nitrophenyl 6-O-benzoyl-2-O,5-C-methylene-β-D-glucopyranoside
  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

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.