Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester | 471930-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6R)-2-hydroxy-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl] acetate
• CAS: 471930-68-4
• 化学式: C₂₄H₂₆Cl₃NO₇
• 分子量: 546.832
• InChiKey: KIZOJJNACYDGBQ-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate
  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 、 四丁基氟化铵 、 溶剂黄146 、 nickel dichloride 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 51.33h， 生成 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+