2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione | 322479-18-5

• 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-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS: 322479-18-5
• 化学式: C₅₇H₅₉NO₁₁S
• 分子量: 966.162
• InChiKey: BNZOGWJCGOJXEU-MQENVRAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  70.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  131.45
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 tetrabutylammonium borohydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙酸酐 为溶剂， 生成 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-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
• 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 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-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