[(3aR,5S,6aR)-6-(1,3-dithian-2-ylidene)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methanol | 257277-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5S,6aR)-6-(1,3-dithian-2-ylidene)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• CAS: 257277-46-6
• 化学式: C₁₂H₁₈O₄S₂
• 分子量: 290.405
• InChiKey: MVSZGJALSQBVIE-SZEHBUNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aR,5S,6aR)-6-(1,3-dithian-2-ylidene)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methanol 在 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 6.17h， 生成 Acetic acid (2S,3R,4R,5S)-2-acetoxy-5-acetoxymethyl-4-[1,3]dithian-2-yl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups

  摘要：

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01814-1
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 4-二甲氨基吡啶 、 正丁基锂 、 四丁基氟化铵 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 [(3aR,5S,6aR)-6-(1,3-dithian-2-ylidene)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
  参考文献：
  名称：

  CHIMERIC RNA WITH MODIFIED BACKBONES: ALTERNATING METHYLENE(METHYLIMINO) LINKED PHOSPHODIESTER BACKBONE OLIGONUCLEOTIDES WITH 2′-OH AND 2′-OMe GROUPS

  摘要：

  Synthesis of a novel ribo-MMI dimer with 2'-OH and 2'-OMe in 5'- and 3'-nucleosides, respectively is presented. The synthesis was accomplished by reductive coupling of 3'-deoxy-3'-C-formyluridine and 2'-O-methyl-5'-O-methylaminouridine via a thioacetal as the key intermediate for the top part of the dimer. Incorporation of ribo-MMI dimers into oligonucleotides increased binding affinity for target RNA.

  DOI：

  10.1081/ncn-100002476

文献信息

• A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups
  作者：Marija Prhavc、George Just*、Balkrishen Bhat、P.Dan Cook、Muthiah Manoharan

  DOI：10.1016/s0040-4039(00)01814-1

  日期：2000.12

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• CHIMERIC RNA WITH MODIFIED BACKBONES: ALTERNATING METHYLENE(METHYLIMINO) LINKED PHOSPHODIESTER BACKBONE OLIGONUCLEOTIDES WITH 2′-OH AND 2′-OMe GROUPS
  作者：Marija Prhavc、Balkrishen Bhat、George Just、P. Dan Cook、Muthiah Manoharan

  DOI：10.1081/ncn-100002476

  日期：2001.3.31

  Synthesis of a novel ribo-MMI dimer with 2'-OH and 2'-OMe in 5'- and 3'-nucleosides, respectively is presented. The synthesis was accomplished by reductive coupling of 3'-deoxy-3'-C-formyluridine and 2'-O-methyl-5'-O-methylaminouridine via a thioacetal as the key intermediate for the top part of the dimer. Incorporation of ribo-MMI dimers into oligonucleotides increased binding affinity for target RNA.