phenyl 2-O-(5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonoyl)-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside | 667463-04-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-(5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonoyl)-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• 英文别名: [(3aS,4R,6S,7R,7aS)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-6-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 667463-04-9
• 化学式: C₅₂H₆₅NO₁₈SSi
• 分子量: 1052.24
• InChiKey: PFRKHCBYADAYTO-BAIGYLLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  258
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-(5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonoyl)-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 溶剂黄146 作用下， 反应 0.5h， 以93%的产率得到phenyl 2-O-(5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonoyl)-6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  摘要：

  An efficient approach was developed for ester-linking the sterically hindered carboxy group of N-acetylneuraminic acid with the secondary hydroxy group at C(2) of galactose. Putative precursors of the glycosidically linked disaccharide Neu5Ac-(2-3)-Gal were prepared.

  DOI：

  10.1023/a:1024803900642
• 作为产物：
  描述：

  2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure 、 phenyl 6-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 N-甲基咪唑 、 苯甲基-2-磺酰三硝基三氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以86%的产率得到phenyl 2-O-(5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosonoyl)-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  摘要：

  An efficient approach was developed for ester-linking the sterically hindered carboxy group of N-acetylneuraminic acid with the secondary hydroxy group at C(2) of galactose. Putative precursors of the glycosidically linked disaccharide Neu5Ac-(2-3)-Gal were prepared.

  DOI：

  10.1023/a:1024803900642