methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside | 507485-63-4

• 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-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside
• 英文别名: (1S,5S,7R,8S,9S)-5-ethenyl-8-methoxy-7-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2,6-dioxabicyclo[3.2.2]nonan-9-ol
• CAS: 507485-63-4
• 化学式: C₃₈H₄₆O₁₀
• 分子量: 662.777
• InChiKey: MJUAYTZBMRAHPZ-FHVVGBOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 在 臭氧 、 sodium chlorite 、 sodium dihydrogenphosphate 、 四丁基碘化铵 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 、 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-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：

  methyl 2,3,6-tri-O-benzyl-4-O-(2,4,7-tri-O-acetyl-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 、 sodium hydroxide 、 草酰氯 、 2-甲基苯磺酸 、 camphor-10-sulfonic acid 、 sodium 、 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 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 82.58h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-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

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.