methyl (methyl 3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside | 630129-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside
• 英文别名: methyl (2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6S)-5-azido-2-(2,2-dimethylpropanoyloxymethyl)-6-methoxy-4-phenylmethoxyoxan-3-yl]oxy-3,4-bis(2,2-dimethylpropanoyloxy)-5-hydroxyoxane-2-carboxylate
• CAS: 630129-64-5
• 化学式: C₃₆H₅₃N₃O₁₄
• 分子量: 751.829
• InChiKey: NGOGNAGTDZLAPO-YVJGARIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (methyl 3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Sodium; (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-5-azido-4-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,4-dihydroxy-5-sulfooxy-tetrahydro-pyran-2-carboxylate
  参考文献：
  名称：

  Development of specific inhibitors for heparin-binding proteins based on the cobra cardiotoxin structure: an effective synthetic strategy for rationally modified heparin-like disaccharides and a trisaccharide

  摘要：

  Recently, a new heparin disaccharide-binding site on the convex side of cobra cardiotoxin (CTX) was identified by NMR spectroscopy and molecular modeling. To further characterize this site two heparin-like disaccharides were synthesized for binding studies with CTX, and a trisaccharide was synthesized for testing the sequence of the disaccharide binding to CTX. Thus six differentially protected monosaccharide building blocks (three L-iduronic acids and three D-glucosamines) were prepared. These include a L-iduronic acid elongation building block namely methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-alpha-L-idopyranosyluronate trichloroacetimidate for which a single-crystal X-ray structure was determined to have M-r = 576.79, a = 9.3098(11) Angstrom alpha = 90degrees, b = 10.3967(12) Angstrom beta = 90degrees, c = 28.026(3) Angstrom gamma = 90degrees, V = 2712.7(6) Angstrom(3), P2(1)2(1)2(1), Z = 4, mu = 0.71073 Angstrom, and R = 0.0378 for 7586 observed reflections. It shows that the molecular structure of the donor is in the C-1(4) conformation with significant 1,3-diaxial interactions between O-1 and O-3 as well as O-2 and O-4. The disaccharides and trisaccharide vary in the degree and position of O- and N-sulfation. The pivaloyl group was used as permanent protecting group of hydroxyl. The levulinoyl group was used as the temporary protecting group to protect the hydroxyl for elongation. Crown Copyright (C) 2005 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.029
• 作为产物：
  描述：

  methyl (methyl 2-O-acetyl-3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以55%的产率得到methyl (methyl 3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside
  参考文献：
  名称：

  A short route to l-iduronic acid building blocks for the syntheses of heparin-like disaccharides

  摘要：

  The effective preparation of differentially protected L-iduronic acid derivatives, as building blocks for the synthesis of heparin-like oligosaccharides, is described in less than nine steps starting from readily available 1,2-O-isopropylidene-6,3-D-glucuronolactone. The pivaloyl group was used as a permanent protecting group of hydroxyl groups. Two heparin-like disaccharides with different sulfation pattern have been prepared by using these L-iduronic acid building blocks. Crown Copyright (C) 2003 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.092

文献信息

• A short route to l-iduronic acid building blocks for the syntheses of heparin-like disaccharides
  作者：Weijun Ke、Dennis M Whitfield、Manjinder Gill、Suzon Larocque、Siu-Hong Yu

  DOI：10.1016/j.tetlet.2003.08.092

  日期：2003.10

  The effective preparation of differentially protected L-iduronic acid derivatives, as building blocks for the synthesis of heparin-like oligosaccharides, is described in less than nine steps starting from readily available 1,2-O-isopropylidene-6,3-D-glucuronolactone. The pivaloyl group was used as a permanent protecting group of hydroxyl groups. Two heparin-like disaccharides with different sulfation pattern have been prepared by using these L-iduronic acid building blocks. Crown Copyright (C) 2003 Published by Elsevier Ltd. All rights reserved.
• Development of specific inhibitors for heparin-binding proteins based on the cobra cardiotoxin structure: an effective synthetic strategy for rationally modified heparin-like disaccharides and a trisaccharide
  作者：Weijun Ke、Dennis M. Whitfield、Jean-Robert Brisson、Gary Enright、Harold C. Jarrell、Wen-guey Wu

  DOI：10.1016/j.carres.2004.11.029

  日期：2005.2

  Recently, a new heparin disaccharide-binding site on the convex side of cobra cardiotoxin (CTX) was identified by NMR spectroscopy and molecular modeling. To further characterize this site two heparin-like disaccharides were synthesized for binding studies with CTX, and a trisaccharide was synthesized for testing the sequence of the disaccharide binding to CTX. Thus six differentially protected monosaccharide building blocks (three L-iduronic acids and three D-glucosamines) were prepared. These include a L-iduronic acid elongation building block namely methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-alpha-L-idopyranosyluronate trichloroacetimidate for which a single-crystal X-ray structure was determined to have M-r = 576.79, a = 9.3098(11) Angstrom alpha = 90degrees, b = 10.3967(12) Angstrom beta = 90degrees, c = 28.026(3) Angstrom gamma = 90degrees, V = 2712.7(6) Angstrom(3), P2(1)2(1)2(1), Z = 4, mu = 0.71073 Angstrom, and R = 0.0378 for 7586 observed reflections. It shows that the molecular structure of the donor is in the C-1(4) conformation with significant 1,3-diaxial interactions between O-1 and O-3 as well as O-2 and O-4. The disaccharides and trisaccharide vary in the degree and position of O- and N-sulfation. The pivaloyl group was used as permanent protecting group of hydroxyl. The levulinoyl group was used as the temporary protecting group to protect the hydroxyl for elongation. Crown Copyright (C) 2005 Published by Elsevier Ltd. All rights reserved.