benzyl 4,6-di-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside | 59104-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4,6-di-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3-acetyloxy-4,6-bis(phenylmethoxy)-5-(phenylmethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 59104-00-6
• 化学式: C₃₂H₃₅NO₉
• 分子量: 577.631
• InChiKey: JAHZNFSGGYXXOU-CWMPKMHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 4,6-di-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal ammonium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以100%的产率得到benzyl 4,6-di-O-acetyl-2-amino-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Selectively O-acylated glycosaminoglycan derivatives

  摘要：

  Glycosaminoglycans, particularly heparin and heparin fragments, were specifically O-acetylated by use of tetrabutylammonium or tributylammonium salts of the anionic polysaccharides, carboxylic acid anhydrides, and 4-dimethylaminopyridine in an homogeneous way in N,N-dimethylformamide. The number of acyl chains introduced on the carbohydrate backbone was determined either after transesterification and quantitative analysis of the butyl esters thus obtained by GLC or by H-1 NMR spectroscopy.

  DOI：

  10.1016/0008-6215(92)85010-w
• 作为产物：
  描述：

  benzyl 3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 生成 benzyl 4,6-di-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Selectively O-acylated glycosaminoglycan derivatives

  摘要：

  Glycosaminoglycans, particularly heparin and heparin fragments, were specifically O-acetylated by use of tetrabutylammonium or tributylammonium salts of the anionic polysaccharides, carboxylic acid anhydrides, and 4-dimethylaminopyridine in an homogeneous way in N,N-dimethylformamide. The number of acyl chains introduced on the carbohydrate backbone was determined either after transesterification and quantitative analysis of the butyl esters thus obtained by GLC or by H-1 NMR spectroscopy.

  DOI：

  10.1016/0008-6215(92)85010-w

文献信息

• Synthesis of anN-Acetylated Heparin Pentasaccharide and its anticoagulant activity in comparison with the heparin pentasaccharide with high anti-factor-Xa activity
  作者：Hans Peter Wessel、Ludvik Labler、Thomas B. Tschopp

  DOI：10.1002/hlca.19890720613

  日期：1989.9.20

  The synthesis of tri-N-acetylated heparin pentasaccharide 2 is described. It was assembled from five suitably blocked monosaccharide units (3–7). Glucuronic-acid building block 4 was prepared from glucose by direct Jones oxidation of the 6-O-trityl derivative 18. The resulting acid 16 was esterified to 17 in large mounts using methyl chloroformate/base. Trimethylsilyl bromide proved to be an excellent

  描述了三-N-乙酰化肝素五糖2的合成。它是从5个合适地保护的单糖单元（组装3 - 7）。通过直接琼斯氧化6- O-三苯甲基衍生物18，由葡萄糖制备葡萄糖醛酸构件4。使用氯甲酸甲酯/碱将所得的酸16大批酯化为17。三甲基甲硅烷基溴化物被证明是水解1--1-烯基糖苷的极佳试剂（19 21）。五糖29通过[2 + 2] +1合成获得的糖基化反应提供了非常好的收率。通过1 H-NMR光谱证实了被保护的寡糖的身份。五糖的顺序解块，Ó -sulfation和Ñ -acetylation得到2，其显示出表现出CA。抗凝血活性比五糖1低600倍。
• WESSEL, HANS PETER;LABLER, LUDVIK;TSCHOPP, THOMAS B., HELV. CHIM. ACTA, 72,(1989) N, C. 1268-1277
  作者：WESSEL, HANS PETER、LABLER, LUDVIK、TSCHOPP, THOMAS B.

  DOI：——

  日期：——