2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate | 471930-63-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[levulinoyl(-3)][Bn(-4)][Bn(-6)]Gal(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl] 4-oxopentanoate
• CAS: 471930-63-9
• 化学式: C₃₄H₃₆Cl₃NO₈
• 分子量: 693.021
• InChiKey: ZWIVCRQDDPMXBB-YGMVDIOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  磷酸二丁酯 、 2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside 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：

  (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol 在 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 达卡巴嗪 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 33.0h， 生成 2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate
  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+

文献信息

• Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3
  作者：Folkert Bosse、Lisa A. Marcaurelle、Peter H. Seeberger

  DOI：10.1021/jo025834+

  日期：2002.9.1

  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.