isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside | 753502-45-3

• 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: isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside
• CAS: 753502-45-3
• 化学式: C₂₇H₄₄O₆Si
• 分子量: 492.728
• InChiKey: XNZNRVVCVIGNRW-YIHAFMAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid
  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 咪唑 、 甲醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 19.5h， 生成 isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-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

• Synthesis of a bicyclic analog of l-iduronic acid adopting the biologically relevant 2 S 0 conformation
  作者：Antonio J. Herrera、Marita T. Beneitez、Luis Amorim、F. Javier Cañada、Jesús Jiménez-Barbero、Pierre Sinaÿ、Yves Blériot

  DOI：10.1016/j.carres.2007.02.025

  日期：2007.9

  The synthesis of a bicyclic analogue of the naturally occurring alpha-L-iduronic acid locked in a biologically active (2)S0 skewboat conformation is disclosed. The desired (2)S0 conformation has been obtained by tethering the C-2 and C-5 carbon atoms of the sugar ring with a dimethyloxy bridge and confirmed by NMR and molecular modeling. The new mimic displays the exact hydroxyl pattern of alpha-L-iduronic

  公开了一种天然存在的α-L-艾杜糖醛酸的双环类似物的合成，该双环类似物被锁定在具有生物活性的（2）SO斜交构象中。通过将糖环的C-2和C-5碳原子与二甲基氧基桥连接在一起，即可获得所需的（2）SO构型，并通过NMR和分子模型确定。与先前报道的双环类似物相比，新的模仿物显示了α-L-异糖醛酸（糖胺聚糖的主要单糖成分）的确切羟基模式，因此代表了后者的更接近的模仿物。