(2R,3S,4R,5R)-3,4-Bis-(2,2-dimethyl-propionyloxy)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 630129-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R)-3,4-Bis-(2,2-dimethyl-propionyloxy)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3S,4R,5R)-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3,4-bis(2,2-dimethylpropanoyloxy)-5-hydroxyoxane-2-carboxylate
• CAS: 630129-50-9
• 化学式: C₂₅H₄₆O₉Si
• 分子量: 518.72
• InChiKey: VZYVLYVRSMNGBV-HPUPVJTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3S,4R,5R)-3,4-Bis-(2,2-dimethyl-propionyloxy)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (dimethylthexylsilyl 2-O-acetyl-3,4-di-O-pivaloyl-α-L-idopyranosid)uronate 、 methyl (dimethylthexylsilyl 2-O-acetyl-3,4-di-O-pivaloyl-β-L-idopyranosid)uronate
  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
• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 在 吡啶 、 咪唑 、 水 、 三乙胺 、 三氟乙酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2R,3S,4R,5R)-3,4-Bis-(2,2-dimethyl-propionyloxy)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  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