2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione | 214467-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]isoindole-1,3-dione
• CAS: 214467-63-7
• 化学式: C₆₄H₆₅NO₁₁S
• 分子量: 1056.29
• InChiKey: UMUFFOWDDVEGKR-PTFZYDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.01
• 重原子数：
  77.0
• 可旋转键数：
  25.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120.45
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 、 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 N-碘代丁二酰亚胺 、 molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

  摘要：

  Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01540-8
• 作为产物：
  描述：

  ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 molecular sieve 、 silver trifluoromethanesulfonate 、 tetrabutylammonium borohydride 、 potassium carbonate 、 二甲基亚砜 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸酐 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

  摘要：

  Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01540-8