N-3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>... | 143544-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>...
• CAS: 143544-41-6
• 化学式: C₉₇H₁₂₁IN₂O₂₉SSi₂
• 分子量: 1994.17
• InChiKey: YLRIOESGSPOBOZ-BPWDGYMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  132.0
• 可旋转键数：
  42.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  370.13
• 氢给体数：
  2.0
• 氢受体数：
  29.0

反应信息

• 作为反应物：
  描述：

  三丁基(苯基甲氧基)锡烷 、 N-3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>... 在 potassium fluoride 、 silver trifluoromethanesulfonate 作用下， 生成 O-benzyl-O-<(benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>...
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007
• 作为产物：
  描述：

  2-(三甲基硅基)乙磺酰胺 、 <(benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-O-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>-1,5-anhydro... 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到N-3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>...
  参考文献：
  名称：

  Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners

  摘要：

  Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLe(x) tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation-rearrangement step allows for the use of minimally protected glycosides as the glycosyl accepters. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Le(x) glycal.

  DOI：

  10.1021/ja00112a007

文献信息

• Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains
  作者：Samuel J. Danishefsky、Koshi Koseki、David A. Griffith、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Takeshi Oriyama

  DOI：10.1021/ja00047a078

  日期：1992.10