phenyl 2,3,4-tri-O-acetyl-6-O-t-butylphenylsilyl-1-thio-β-D-galactopyranoside | 862253-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-acetyl-6-O-t-butylphenylsilyl-1-thio-β-D-galactopyranoside
• CAS: 862253-08-5
• 化学式: C₃₄H₄₀O₈SSi
• 分子量: 636.838
• InChiKey: UGUUAPHBAOQBEJ-CYEGLCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-6-O-t-butylphenylsilyl-1-thio-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 4 A molecular sieve 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 以88%的产率得到2-(trimethylsilyl)ethyl-2,3,4-tri-O-acetyl-6-O-t-butyldiphenylsilyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Two Lewis^XTrisaccharides Using Regiospecific Glycosylation Reactions

  摘要：

  Synthesis of two Lewis(x) trisaccharides, namely, 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside and 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-t-butyldiphenylsilyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside, has been achieved using a regiospecific glycosylation strategy under NIS-TfOH activation. Two trisaccharides were prepared from monosaccharides without any protecting group manipulation.

  DOI：

  10.1081/car-200058529
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 phenyl 2,3,4-tri-O-acetyl-6-O-t-butylphenylsilyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Two Lewis^XTrisaccharides Using Regiospecific Glycosylation Reactions

  摘要：

  Synthesis of two Lewis(x) trisaccharides, namely, 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside and 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-t-butyldiphenylsilyl-beta-D-galactopyranosyl-(1 -> 4)-6-O-benzyl-2-deoxy-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-phthalimido-beta-D-glucopyranoside, has been achieved using a regiospecific glycosylation strategy under NIS-TfOH activation. Two trisaccharides were prepared from monosaccharides without any protecting group manipulation.

  DOI：

  10.1081/car-200058529