isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside | 612841-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-2-ethenyl-4-phenylmethoxy-6-propan-2-yloxyoxan-2-yl]methyl acetate
• CAS: 612841-85-7
• 化学式: C₂₄H₃₂O₉
• 分子量: 464.513
• InChiKey: VZOYPUUBUNDLNM-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside 在 甲醇 、 sodium 作用下， 反应 16.0h， 生成 (2R,3S,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-isopropoxy-2-vinyl-tetrahydro-pyran-3,5-diol
  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,3R,4S,5S,6R)-4-Benzyloxy-6-hydroxymethyl-6-vinyl-tetrahydro-pyran-2,3,5-triol 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-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

• RCM as a tool to freeze conformation of monosaccharides: synthesis of a β-mannopyranoside mimic adopting a conformation close to the biologically relevant B2,5 boat
  作者：Luis Amorim、Dolores Díaz、Luis P. Calle-Jiménez、Jesús Jiménez-Barbero、Pierre Sinaÿ、Yves Blériot

  DOI：10.1016/j.tetlet.2006.10.046

  日期：2006.12

  The synthesis of a P-D-mannopyranoside analog, fully identical to the naturally occurring D-mannopyranose in terms of hydroxyl pattern, and displaying a skew-boat conformation close to a B-2,B-5 boat strongly believed to be adopted by the oxycarbenium transition state during glycosidic bond cleavage of beta-mannane by family 26 beta-mannanase, is described. The conformationally locked analog has been obtained by tethering the C-2 and C-5 carbon atoms of the sugar ring with a three carbon bridge using RCM methodology. Conformation of the mannose analog has been confirmed by NMR and molecular modelling. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.