dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside | 471930-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl] acetate
• CAS: 471930-67-3
• 化学式: C₃₂H₄₄Cl₃NO₇Si
• 分子量: 689.148
• InChiKey: IDDYSHNBSIZQDG-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以91%的产率得到Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+
• 作为产物：
  描述：

  3-O-Acetyl-4,6-di-O-benzyl-D-galactal 在 sodium tetrahydroborate 、 sodium azide 、 ammonium cerium(IV) nitrate 、 nickel dichloride 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 31.33h， 生成 dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
  参考文献：
  名称：

  Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3

  摘要：

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

  DOI：

  10.1021/jo025834+