3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranose | 223591-10-4

• 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: 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranose
• 英文别名: (2R,3S,4S)-3-benzyloxy-4-benzyloxymethyl-2-formyl-4-hydroxytetrahydrofuran；(2R,3S,4S)-4-hydroxy-3-phenylmethoxy-4-(phenylmethoxymethyl)oxolane-2-carbaldehyde
• CAS: 223591-10-4
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: NACHHSULPPBYJO-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranose 在 镍 四甲基乙二胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 生成 5-[(1R)-3,5-di-O-benzyl-2-O,4-C-methylene-D-ribitol-1-yl]oxazole
  参考文献：
  名称：

  有效合成2'，4'-BNA修饰的C-核苷

  摘要：

  通过使用四氢呋喃甲醛1与镁或锂衍生物的偶联反应，完成了具有2'- O，4'- C-亚甲基桥连核酸（2'，4'-BNA）修饰的某些C-核苷的有效合成芳香杂环，然后进行Mitsunobu环化。此外，通过1 H NMR谱和X射线晶体学清楚地表明，合成的C-核苷中的糖构象独立于核碱基，被固定为N-形式。

  DOI：

  10.1016/s0040-4020(02)00226-0
• 作为产物：
  描述：

  ((3aS,6R,6aR)-6-甲氧基-2,2-二甲基四氢呋喃并[3,4-d][1,3]二氧杂环戊烯-4,4-二基)二甲醇 在 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 水 、 sodium hexamethyldisilazane 、 四氯化钛 、 sodium hydride 、 sodium cyanoborohydride 、 三乙胺 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranose
  参考文献：
  名称：

  具有2,5-二氧杂双环[2.2.1]庚烷环系统的构象锁定的C-核苷的合成

  摘要：

  通过四氢呋喃甲醛1与芳族杂环的锂和镁衍生物的偶联反应，成功地合成了具有2,5-二氧杂双环[2.2.1]庚烷环系统的新型C-核苷。

  DOI：

  10.1016/s0040-4039(99)01998-x

文献信息

• Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-d-ribofuranoside: a key synthon towards α-LNA
  作者：Poul Nielsen、Jesper Wengel

  DOI：10.1039/a806817h

  日期：——

  A bicyclic thiofuranoside (phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside) was efficiently synthesized and introduced as the key synthon in a method for convergent synthesis of α- and β-LNA nucleosides; acid-induced ring-opening reactions of the corresponding bicyclic methyl furanoside are also described.

  一种双环硫呋喃苷（苯基3,5-二-O-苄基-2-O,4-C-亚甲基-β-D-核糖呋喃苷）被高效合成并作为α-和β-LNA核苷的聚合合成中的关键合成物引入；还描述了相应双环甲基呋喃苷的酸诱导开环反应。
• 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.
• 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.
• Triplex formation by an oligonucleotide containing conformationally locked C-nucleoside, 5-(2-O,4-C-methylene-β-d-ribofuranosyl)oxazole
  作者：Satoshi Obika、Yoshiyuki Hari、Ken-ichiro Morio、Takeshi Imanishi

  DOI：10.1016/s0040-4039(99)02052-3

  日期：2000.1

  The tripler-forming ability of oligonucleotide analogues containing conformationally locked C-nucleosides, 5-(2-O,4-C-methylene- beta-D-ribofuranosyl)oxazole or its 2-phenyl congener, towards a purine sequence of duplex DNA with a single C.G base pair interruption is studied. (C) 1999 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：——