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)>... | 143508-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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)>...
• CAS: 143508-68-3
• 化学式: C₁₂₀H₁₄₀N₂O₃₃SSi₂
• 分子量: 2226.66
• InChiKey: QXHIBOWSFCFTJM-UAURYIEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  158.0
• 可旋转键数：
  47.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  418.05
• 氢给体数：
  3.0
• 氢受体数：
  33.0

反应信息

• 作为产物：
  描述：

  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 silver tetrafluoroborate 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到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：

  Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains

  摘要：

  DOI：

  10.1021/ja00047a078

文献信息

• Application of Glycals to the Synthesis of Oligosaccharides: Convergent Total Syntheses of the Lewis X Trisaccharide Sialyl Lewis X Antigenic Determinant and Higher Congeners
  作者：Samuel J. Danishefsky、Jacquelyn Gervay、John M. Peterson、Frank E. McDonald、Koshi Koseki、David A. Griffith、Takeshi Oriyama、Stephen P. Marsden

  DOI：10.1021/ja00112a007

  日期：1995.2

  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.