(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran | 223591-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran
• 英文别名: [(2S,3S,4S)-4-hydroxy-3-phenylmethoxy-4-(phenylmethoxymethyl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 223591-06-8
• 化学式: C₂₇H₃₀O₇S
• 分子量: 498.597
• InChiKey: OYOZATIDKAVPQN-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran 在 palladium dihydroxide 4-二甲氨基吡啶 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.0h， 生成 (2S,3S,4S)-3-hydroxy-4-hydroxymethyl-3-O,O-(hydroxymethyl)-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-((p-toluenesulfonyloxy)methyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of Abasic Locked Nucleic Acid and Two seco-LNA Derivatives and Evaluation of Their Hybridization Properties Compared with Their More Flexible DNA Counterparts

  摘要：

  To investigate the structural basis of the unique hybridization properties of LNA (locked nucleic acid) three novel LNA derivatives with modified carbohydrate parts were synthesized and evaluated with respect to duplex stabilities. The abasic LNA monomer (X(L), Figure 1) with the rigid carbohydrate moiety of LNA but no nucleobase attached showed no enhanced duplex stabilities compared to its more flexible abasic DNA counterpart (X, Figure 1). These results suggest that the exceptional hybridization properties of LNA primarily originate from improved intrastrand nucleobase stacking and not backbone preorganization. Two monocyclic seco-LNA derivatives, obtained by cleavage of the C1'-O4' bond of an LNA monomer or complete removal of the O4'-furanose oxygen atom (Z(L) and dZ(L), respectively, Figure 1), were compared to their acyclic DNA counterpart (Z, Figure 1). Even though they are more constrained than Z, the seco-LNA derivatives Z(L) and dZ(L) destabilize duplex formation even more than the flexible seco-DNA monomer Z.

  DOI：

  10.1021/jo000275x
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-methanesulfonyloxymethyl-α-D-ribofuranose 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.83h， 生成 (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-(p-toluenesulfonyl)oxymethyl-4-hydroxytetrahydrofuran
  参考文献：
  名称：

  Synthesis of Abasic Locked Nucleic Acid and Two seco-LNA Derivatives and Evaluation of Their Hybridization Properties Compared with Their More Flexible DNA Counterparts

  摘要：

  To investigate the structural basis of the unique hybridization properties of LNA (locked nucleic acid) three novel LNA derivatives with modified carbohydrate parts were synthesized and evaluated with respect to duplex stabilities. The abasic LNA monomer (X(L), Figure 1) with the rigid carbohydrate moiety of LNA but no nucleobase attached showed no enhanced duplex stabilities compared to its more flexible abasic DNA counterpart (X, Figure 1). These results suggest that the exceptional hybridization properties of LNA primarily originate from improved intrastrand nucleobase stacking and not backbone preorganization. Two monocyclic seco-LNA derivatives, obtained by cleavage of the C1'-O4' bond of an LNA monomer or complete removal of the O4'-furanose oxygen atom (Z(L) and dZ(L), respectively, Figure 1), were compared to their acyclic DNA counterpart (Z, Figure 1). Even though they are more constrained than Z, the seco-LNA derivatives Z(L) and dZ(L) destabilize duplex formation even more than the flexible seco-DNA monomer Z.

  DOI：

  10.1021/jo000275x

文献信息

• Kvaerno, Lisbet; Wengel, Jesper, Chemical Communications, 1999, # 7, p. 657 - 658
  作者：Kvaerno, Lisbet、Wengel, Jesper

  DOI：——

  日期：——
• Synthesis of Abasic Locked Nucleic Acid and Two <i>seco</i>-LNA Derivatives and Evaluation of Their Hybridization Properties Compared with Their More Flexible DNA Counterparts
  作者：Lisbet Kværnø、Ravindra Kumar、Britta M. Dahl、Carl Erik Olsen、Jesper Wengel

  DOI：10.1021/jo000275x

  日期：2000.8.1

  To investigate the structural basis of the unique hybridization properties of LNA (locked nucleic acid) three novel LNA derivatives with modified carbohydrate parts were synthesized and evaluated with respect to duplex stabilities. The abasic LNA monomer (X(L), Figure 1) with the rigid carbohydrate moiety of LNA but no nucleobase attached showed no enhanced duplex stabilities compared to its more flexible abasic DNA counterpart (X, Figure 1). These results suggest that the exceptional hybridization properties of LNA primarily originate from improved intrastrand nucleobase stacking and not backbone preorganization. Two monocyclic seco-LNA derivatives, obtained by cleavage of the C1'-O4' bond of an LNA monomer or complete removal of the O4'-furanose oxygen atom (Z(L) and dZ(L), respectively, Figure 1), were compared to their acyclic DNA counterpart (Z, Figure 1). Even though they are more constrained than Z, the seco-LNA derivatives Z(L) and dZ(L) destabilize duplex formation even more than the flexible seco-DNA monomer Z.