(1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane | 223590-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: (1S,4R,7S)-3-methoxy-7-phenylmethoxy-1-(phenylmethoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS: 223590-98-5
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: MHFIXIZPCXNGLH-NZKBUGBHSA-N

物化性质

• 沸点：
  473.7±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 四丁基氟化铵 、 氢气 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 111.5h， 生成 (2S,3S,4S)-3-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-4-((4,4'-dimethoxytrityl)oxymethyl)-2-((thymin-1-yl)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：

  1,2-O-(异丙亚基)-4-C-[(苯基甲氧基)甲基]-3-O-(苯基甲基)-beta-L-来苏呋喃糖 在 盐酸 、 sodium hydride 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  A New Synthetic Approach Towards α- and β-LNA (Locked Nucleic Acids)

  摘要：

  A bicyclo[2.2.1] phenyl thioglycoside was efficiently synthesised and introduced as the key synthon in a novel method for convergent synthesis of beta-LNA-nucleosides as well as their alpha-configurated isomers. An acid-induced ring-opening reaction on the corresponding bicyclo[2.2.1] methyl furanoside is also described.

  DOI：

  10.1080/15257779908041546

文献信息

• Recognition of T·A interruption by 2′,4′-BNAs bearing heteroaromatic nucleobases through parallel motif triplex formation
  作者：Satoshi Obika、Hiroyasu Inohara、Yoshiyuki Hari、Takeshi Imanishi

  DOI：10.1016/j.bmc.2007.12.043

  日期：2008.3.15

  2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA) monomers bearing novel unnatural nucleobases, 4-(3-benzamidophenyl)-2-pyridone and 2-(N-methylbenzamido)thiazole, were synthesized and successfully incorporated into oligonucleotides. UV melting experiments showed that the corresponding oligonucleotide derivatives formed stable triplexes with dsDNA targets even in the presence of a T center dot A interruption. (C) 2007 Elsevier Ltd. All rights reserved.
• Kvaerno, Lisbet; Wengel, Jesper, Chemical Communications, 1999, # 7, p. 657 - 658
  作者：Kvaerno, Lisbet、Wengel, Jesper

  DOI：——

  日期：——