| 174004-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 174004-00-3
• 化学式: C₄₃H₇₈INO₁₂SSi₃
• 分子量: 1044.32
• InChiKey: KRGWSRJNHUFATE-RJFXXRGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.64
• 重原子数：
  61.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  157.31
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  、 乙硫醇 在 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-[(2S,3R,4R,5R,6R)-4-[[(3aS,4R,6R,7R,7aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-oxo-4-[tri(propan-2-yl)silyloxymethyl]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-2-ethylsulfanyl-5-hydroxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of Asialo GM₁. New Insights in the Application of Sulfonamidoglycosylation in Oligosaccharide Assembly:  Subtle Proximity Effects in the Stereochemical Governance of Glycosidation

  摘要：

  The total synthesis of asialo GM(1) (1a) has been accomplished, Using related chemistry, the methyl glycoside of the asialo compound (1b) has also been synthesized. These kinds of compounds have been identified as potential ligands for bacterial and viral infection sites, A simpler structure, which hits also been identified for its infection attracting structure in the context of glycopeptides and glycolipids (methyl glycoside 2), has also been synthesized. The key common phase in the syntheses involves the sulfonamidoglycosidation reaction which is used to create a beta-linkage leading to a galNAc residue joined to the C-4 hydroxyl group of a galactose unit either as a monosaccharide (see compound 2) or as C-4' in the contest of a lactosyl moiety, During the course of these studies there was encountered an unusual "proximal hydroxyl" directing effect. Thus, when C-4 on the galactose ring of an azaglycosylating donor bears a free hydroxyl (see, for instance, compound 13), beta-glycoside formation predominates. When this hydroxyl group is blocked, the process tends in the direction of alpha-glycoside formation (see compound 32), These findings were explained as arising from a critical intramolecular hydrogen bond between the C-4 axial hydroxyl of the galactose donor and its proximal pyranosidal ring oxygen. This interaction stabilizes conformations from which beta-glycosidation predominates.

  DOI：

  10.1021/ja9724957
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 咪唑 、 iodonium(di-γ-collidine) perchlorate 、 米帕明 、 氨 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Synthesis of Asialo GM₁. New Insights in the Application of Sulfonamidoglycosylation in Oligosaccharide Assembly:  Subtle Proximity Effects in the Stereochemical Governance of Glycosidation

  摘要：

  The total synthesis of asialo GM(1) (1a) has been accomplished, Using related chemistry, the methyl glycoside of the asialo compound (1b) has also been synthesized. These kinds of compounds have been identified as potential ligands for bacterial and viral infection sites, A simpler structure, which hits also been identified for its infection attracting structure in the context of glycopeptides and glycolipids (methyl glycoside 2), has also been synthesized. The key common phase in the syntheses involves the sulfonamidoglycosidation reaction which is used to create a beta-linkage leading to a galNAc residue joined to the C-4 hydroxyl group of a galactose unit either as a monosaccharide (see compound 2) or as C-4' in the contest of a lactosyl moiety, During the course of these studies there was encountered an unusual "proximal hydroxyl" directing effect. Thus, when C-4 on the galactose ring of an azaglycosylating donor bears a free hydroxyl (see, for instance, compound 13), beta-glycoside formation predominates. When this hydroxyl group is blocked, the process tends in the direction of alpha-glycoside formation (see compound 32), These findings were explained as arising from a critical intramolecular hydrogen bond between the C-4 axial hydroxyl of the galactose donor and its proximal pyranosidal ring oxygen. This interaction stabilizes conformations from which beta-glycosidation predominates.

  DOI：

  10.1021/ja9724957

文献信息

• A total synthesis of a stage specific pentasaccharide embryogenesis marker
  作者：Tae Kyo Park、In Jong Kim、Samuel J. Danishefsky

  DOI：10.1016/0040-4039(95)01962-h

  日期：1995.12

  A thioglycoside coupling mediated by methyl triflate was used to generate Stage Specific Embryonic Antigen-3.