methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside | 1054659-84-5

• 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-O-acetyl-6-deoxy-3-O-methyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5S,6S)-6-ethenyl-5-hydroxy-4-methoxy-2-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-[2-(4-methylphenyl)sulfonyloxyethyl]oxan-3-yl] acetate
• CAS: 1054659-84-5
• 化学式: C₄₇H₅₆O₁₄S
• 分子量: 877.019
• InChiKey: YMESFYWZNYUJRR-NEOGGGBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-7-O-tosyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside 在 sodium hydroxide 、 camphor-10-sulfonic acid 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.33h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-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：

  Acetic acid (2R,3S,4S,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-yl ester 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-6-deoxy-3-O-methyl-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