ethyl 2-O-[1-O-methyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranos-3-yloxycarbonylpropanoyl]-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 259871-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-[1-O-methyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranos-3-yloxycarbonylpropanoyl]-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• CAS: 259871-12-0
• 化学式: C₅₂H₇₆O₁₄SSi₂
• 分子量: 1013.4
• InChiKey: IOHNGKNAMUNDPB-ZTKRHAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  69.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  155.9
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-[1-O-methyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranos-3-yloxycarbonylpropanoyl]-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 molecular sieve 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以23%的产率得到methyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->6)-3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranoside-2,2'-succinate
  参考文献：
  名称：

  Prearranged Glycosides. Part 8. Intramolecular α-Galactosylation Via Succinoyl Tethered Glycosides

  摘要：

  Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding alpha-(1-->4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

  DOI：

  10.1080/07328309908544056
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 ethyl 2-O-[1-O-methyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranos-3-yloxycarbonylpropanoyl]-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Prearranged Glycosides. Part 8. Intramolecular α-Galactosylation Via Succinoyl Tethered Glycosides

  摘要：

  Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding alpha-(1-->4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

  DOI：

  10.1080/07328309908544056