N-[(2S,3R,4R,5S,6R)-2-[3-[bis[3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropyl]-phenylsilyl]propylsulfanyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | 1242449-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-[3-[bis[3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropyl]-phenylsilyl]propylsulfanyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1242449-38-2
• 化学式: C₃₉H₆₅N₃O₁₅S₃Si
• 分子量: 940.24
• InChiKey: PBJJAEKBOXLBIE-TZOHVRFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.46
• 重原子数：
  61
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  373
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  尿苷 5’-二二氧磷基半乳糖二钠盐 、 N-[(2S,3R,4R,5S,6R)-2-[3-[bis[3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropyl]-phenylsilyl]propylsulfanyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 在 β-1,4-galactosyl transferase 、 α-lactoalbumin 、 magnesium chloride 作用下， 反应 72.0h， 以92.4%的产率得到N-[(2S,3R,4R,5S,6R)-2-[3-[bis[3-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpropyl]-phenylsilyl]propylsulfanyl]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
  参考文献：
  名称：

  Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches

  摘要：

  An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta 1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha 2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.066
• 作为产物：
  描述：

  N-[(2R,3R,4R,5S,6R)-2-[3-[bis[3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl]-phenylsilyl]propoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 在 甲醇 、 sodium methylate 、 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以97%的产率得到N-[(2S,3R,4R,5S,6R)-2-[3-[bis[3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropyl]-phenylsilyl]propylsulfanyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  参考文献：
  名称：

  Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches

  摘要：

  An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta 1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha 2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.066