5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-... | 221664-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-...
• CAS: 221664-01-3
• 化学式: C₁₈₃H₃₀₆O₄₂Si₁₀
• 分子量: 3459.27
• InChiKey: SZCHNWQLJVAVLA-SHXKZENNSA-N

反应信息

• 作为反应物：
  描述：

  5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-... 在 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以86%的产率得到5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-6...
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 17, Synthesis and Characterization of a Hexadecamer: Evidence for the Essential Structural Role of the Intramolecular, Interresidue C(3)−OH⋅⋅⋅O−C(5) Hydrogen Bond in Celluloses

  摘要：

  The hexadecamer 63 dissolves readily in DMSO and shows no sign of association, in agreement with the essential structural role of the intramolecular, interresidue C(3)-OH ... O-C(5) H-bond of celluloses, MM3 Calculations predict a rod-like shape for the cello-oligosaccharides In agreement with this, nanocrystalline domains of parallel chains are observed by high-resolution electron microscopy (HREM) for 54 and 63 on carbon-coated copper grids. For the synthesis of the hexadecamer 54, we studied the influence of protecting groups on the cross-coupling of acetyleno-oligosaccharides and on their solubility (Scheme 2). The octamer 12 derived from the minimally O-protected monomer 2 is insoluble, while the methoxymethyl- and triisopropysilyl-protected hexadecamer 54 prepared in twelve steps from the dimer 41 (Scheme 4), is readily soluble in a variety of solvents. O- and C-deprotection of 54 led in four steps and in 76% yield to the hexadecamer 63 (Schemes 5 and 6). There is only a small difference of spectroscopic properties between the protected octamer 50 and hexadecamer 54, and, similarly, between the unprotected octamer 64 and hexadecamer 63 (Fig. 3).

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<198::aid-hlca198>3.0.co;2-y
• 作为产物：
  描述：

  5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<(3-hydroxy-1,1-dimethylpropyl)dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-6-O-(triisopropylsilyl)-D... 、 5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy... 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 P(fur)3 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以80%的产率得到5,9-anhydro-1,2,3,4,8-pentadeoxy-8-C-<<<1,1-dimethyl-3-<(tetrahydro-2H-pyran-2-yl)oxy>propyl>dimethylsilyl>ethynyl>-7,10-bis-O-(methoxymethyl)-6-O-(triisopropylsilyl)-D-glycero-D-gulo-deca-1,3-diynitol-1-yl-(1->8-C)-5,9-anhydro-1,2,3,4,8-pentadeoxy-...
  参考文献：
  名称：

  Oligosaccharide Analogues of Polysaccharides, Part 17, Synthesis and Characterization of a Hexadecamer: Evidence for the Essential Structural Role of the Intramolecular, Interresidue C(3)−OH⋅⋅⋅O−C(5) Hydrogen Bond in Celluloses

  摘要：

  The hexadecamer 63 dissolves readily in DMSO and shows no sign of association, in agreement with the essential structural role of the intramolecular, interresidue C(3)-OH ... O-C(5) H-bond of celluloses, MM3 Calculations predict a rod-like shape for the cello-oligosaccharides In agreement with this, nanocrystalline domains of parallel chains are observed by high-resolution electron microscopy (HREM) for 54 and 63 on carbon-coated copper grids. For the synthesis of the hexadecamer 54, we studied the influence of protecting groups on the cross-coupling of acetyleno-oligosaccharides and on their solubility (Scheme 2). The octamer 12 derived from the minimally O-protected monomer 2 is insoluble, while the methoxymethyl- and triisopropysilyl-protected hexadecamer 54 prepared in twelve steps from the dimer 41 (Scheme 4), is readily soluble in a variety of solvents. O- and C-deprotection of 54 led in four steps and in 76% yield to the hexadecamer 63 (Schemes 5 and 6). There is only a small difference of spectroscopic properties between the protected octamer 50 and hexadecamer 54, and, similarly, between the unprotected octamer 64 and hexadecamer 63 (Fig. 3).

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<198::aid-hlca198>3.0.co;2-y