methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside | 507485-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside
• 英文别名: (5aS,7R,8R,9R,9aS)-5a-ethenyl-9-methoxy-7-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2,2-dimethyl-4,5,7,8,9,9a-hexahydropyrano[3,2-d][1,3]dioxepin-8-ol
• CAS: 507485-53-2
• 化学式: C₄₁H₅₂O₁₁
• 分子量: 720.857
• InChiKey: YEFRLRCONVKTSB-IJARUQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 camphor-10-sulfonic acid 、 三乙基硼氢化锂 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Further Evidence for the Critical Role of a Non-Chair Conformation of L-Iduronic Acid in the Activation of Antithrombin

  摘要：

  L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosammoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an Liduronic acid residue conformationally forced to exist within a restricted arc (S-2(0) reversible arrow B-2,B-5 reversible arrow S-5(1)) of the overall pseudorotational circle. We could thus demonstrate that the S-2(0) conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to S-2(0) and clearly explains how the unique conformational behavior Of L-iduronic acid is the key to heparin's interaction with AT-III.

  DOI：

  10.1002/1099-0690(200211)2002:21<3595::aid-ejoc3595>3.0.co;2-f
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 、 sodium 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Further Evidence for the Critical Role of a Non-Chair Conformation of L-Iduronic Acid in the Activation of Antithrombin

  摘要：

  L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosammoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an Liduronic acid residue conformationally forced to exist within a restricted arc (S-2(0) reversible arrow B-2,B-5 reversible arrow S-5(1)) of the overall pseudorotational circle. We could thus demonstrate that the S-2(0) conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to S-2(0) and clearly explains how the unique conformational behavior Of L-iduronic acid is the key to heparin's interaction with AT-III.

  DOI：

  10.1002/1099-0690(200211)2002:21<3595::aid-ejoc3595>3.0.co;2-f

文献信息

• Further Evidence for the Critical Role of a Non-Chair Conformation of L-Iduronic Acid in the Activation of Antithrombin
  作者：José Kovensky、Jean-Maurice Mallet、Jacques Esnault、Pierre-Alexandre Driguez、Philippe Sizun、Jean-Pascal Hérault、Jean-Marc Herbert、Maurice Petitou、Pierre Sinaÿ

  DOI：10.1002/1099-0690(200211)2002:21<3595::aid-ejoc3595>3.0.co;2-f

  日期：2002.11

  L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosammoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an Liduronic acid residue conformationally forced to exist within a restricted arc (S-2(0) reversible arrow B-2,B-5 reversible arrow S-5(1)) of the overall pseudorotational circle. We could thus demonstrate that the S-2(0) conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to S-2(0) and clearly explains how the unique conformational behavior Of L-iduronic acid is the key to heparin's interaction with AT-III.