(2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran | 223590-99-6

• 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-hydroxymethyl-4-hydroxytetrahydrofuran
• 英文别名: (3S,4S,5S)-5-(hydroxymethyl)-4-phenylmethoxy-3-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 223590-99-6
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: DMFILMOQHZDASS-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-4-hydroxytetrahydrofuran 在 吡啶 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 Pd(OH)2/C, 20% 、 potassium carbonate 、 三乙胺 、 环己烯 、 二异丙基铵盐四氮唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 57.08h， 生成 1-allyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl}benzene
  参考文献：
  名称：

  Base-pair recognition ability of hydroxyphenyl nucleobases in parallel triplex DNA

  摘要：

  Oligonucleotides containing 2'-deoxyribonucleotides bearing hydroxyphenyl nucleobases or their 2',4'-BNA-modified analogs were synthesized, and the triplex-forming ability of their oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. Results showed that 2'-deoxyribonucleotide bearing 2'-hydroxyphenyl nucleobase could be recognized by a dUA base pair while no affinity to a TA base pair was observed. The,4'-BNA modification led to a further increase in the binding affinity to a dUA base pair. The,4'-BNA bearing 3-hydroxyphenyl nucleobase showed moderate binding affinity to a TA base pair, but without selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.107
• 作为产物：
  描述：

  methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside 在 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.83h， 生成 (2S,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-hydroxymethyl-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

• Triplex-forming enhancement with high sequence selectivity by single 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA) modification
  作者：Satoshi Obika、Yoshiyuki Hari、Tomomi Sugimoto、Mitsuaki Sekiguchi、Takeshi Imanishi

  DOI：10.1016/s0040-4039(00)01607-5

  日期：2000.11

  Tripler-forming ability of the oligonucleotides containing one 2'-O,3'-C-methyleneribonucleic acid (2',4'-BNA) unit was investigated by measurement of the melting temperature (T-m), and the 2',4'-BNA modification promoted the marked tripler stabilization in a highly sequence-selective manner. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kvaerno, Lisbet; Wengel, Jesper, Chemical Communications, 1999, # 7, p. 657 - 658
  作者：Kvaerno, Lisbet、Wengel, Jesper

  DOI：——

  日期：——