((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol | 69832-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol
• 英文别名: 3-deoxy-3-C-(hydroxymethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-deoxy-3-(hydroxymethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-deoxy-3-hydroxymethyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；[(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]methanol
• CAS: 69832-48-0
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: RUYAPXWKJMZDCJ-KAMPLNKDSA-N

物化性质

• 沸点：
  352.7±42.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose
  参考文献：
  名称：

  A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity

  摘要：

  Two ring-expanded analogues (compounds 2 and 3) of the anti-HIV fermentation product oxetanocin A (1) were synthesized from commercially available diacetone D-glucose. Antiviral testing against HIV in ATH8 cells revealed that the ring-expanded analogue 2 possessed a similar activity profile as oxetanocin A. Neither compound, however, was capable of providing full protection to the cells against HIV infection. The isomeric ring-expanded analogue 3 was totally devoid of anti-HIV activity. Molecular modeling suggested that while oxetanocin A and compounds 2 and 3 share a large common substructure with the potent anti-HIV drug, dideoxyadenosine (ddA), the extra hydroxymethyl substituent may contribute negatively to the binding of these molecules to a critical enzyme. The negative contribution may be less important in oxetanocin and isomer 2 than in isomer 3. From these studies it would appear that both oxetane and tetrahydrofuran rings are equivalent templates to support the adenine base in terms of anti-HIV activity.

  DOI：

  10.1021/jm00105a054
• 作为产物：
  描述：

  双丙酮葡萄糖 在 sodium hypochlorite 、 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 dimethyl sulfide borane 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol
  参考文献：
  名称：

  反义寡核苷酸构建物中氧杂双环核苷膦酸盐作为核苷酸间磷酸替代物的构想和合成。

  摘要：

  实现了包含全氢呋喃吡喃核单元的新型氧杂双环核苷膦酸酯的立体控制合成。它以5'–3'膦酸酯-磷酸插入物的形式掺入寡核苷酸序列中，并测量了所得双链体的稳定性。设计氧杂双环核苷骨架，以限制围绕天然核苷的角度γ，δ和ε旋转。

  DOI：

  10.1021/acs.orglett.8b02233

文献信息

• Useful Intermediates, 3-<i>C</i>-Dichloromethyl Furanose Derivatives, for the Synthesis of Branched-Chain Functionalized Sugars
  作者：Ken-ichi Sato、Katsuhiko Suzuki、Miyuki Ueda、Yasuhiro Kajihara、Hiroyuki Hori

  DOI：10.1246/bcsj.70.225

  日期：1997.1

  azido at the quaternary carbon, were stereoselectively prepared in good yield via the same intermediary 3-C-,3-O-chloromethylene- or 3-C-dichloromethyl-1,2 : 5,6-di-O-isopropylidene-α-D-furanose derivatives.

  通过相同的中间体 3-C-,3-O-氯亚甲基-或在季碳上具有重要的功能，如羟基、氢、氯或叠氮基，以良好的收率立体选择性地制备了一些新型支链功能化糖。 3-C-二氯甲基-1,2 : 5,6-二-O-异亚丙基-α-D-呋喃糖衍生物。
• A Novel Reagent for the Synthesis of Branched-chain Functionalized Sugars. Dichloromethyllithium
  作者：Ken-ichi Sato、Katsuhiko Suzuki、Miyuki Ueda、Masaftimi Katayama、Yasuhiro Kajihara

  DOI：10.1246/cl.1991.1469

  日期：1991.8

  A few novel branched-chain functionalized sugars, which have important functions such as hydroxyl, hydro, chloro, or azido at quaternary carbon were prepared in good yield via the same intermediary spiro chloroepoxide derivative by use of dichloromethyllithium.

  使用二氯甲基锂通过相同的中间体螺环氯环氧化物衍生物以良好的收率制备了一些新型支链官能化糖，它们具有重要的功能，例如季碳上的羟基、氢、氯或叠氮基。
• Synthesis and biological evaluation of thymine nucleosides fused with 3′,4′-tetrahydrofuran ring
  作者：Myong Jung Kim、Hea Ok Kim、Hee-Doo Kim、Joong Hyup Kim、Lak Shin Jeong、Moon Woo Chun

  DOI：10.1016/s0960-894x(03)00730-3

  日期：2003.10

  The pyrimidine nucleosides fused with 3',4'-tetrahydrofuran ring were successfully synthesized, starting from 1,2;5,6-di-O-isopropylidene-D-glucose and assayed for antiviral activities against HIV-1, HIV-2, EMCV, Cox. B3 and VSV. Thymine analogue (5) and its corresponding 2'-deoxy analogue (6) exhibited high cytotoxicity instead of giving antiviral activities.

  从1,2; 5,6-di-O-异亚丙基-D-葡萄糖开始，成功合成了与3'，4'-四氢呋喃环稠合的嘧啶核苷，并测定了其对HIV-1，HIV-2， EMCV，考克斯。B3和VSV。胸腺嘧啶类似物（5）及其相应的2'-脱氧类似物（6）表现出高细胞毒性，而不具有抗病毒活性。
• Oligomeric compounds having at least one neutrally linked terminal bicyclic nucleoside
  申请人：Seth Punit P.

  公开号：US09290534B2

  公开（公告）日：2016-03-22

  The present disclosure describes oligomeric compounds having at least one bicyclic nucleoside attached to the 3′ or 5′ termini by a neutral internucleoside linkage and methods of using the oligomeric compounds. In some embodiments, the oligomeric compounds provided herein hybridize to a portion of a target RNA resulting in loss of normal function of the target RNA.

  本公开描述了具有至少一个双环核苷酸连接到3′或5′末端的寡聚化合物，其通过中性核苷酸间连接，并描述了使用这些寡聚化合物的方法。在某些实施例中，本文提供的寡聚化合物与靶RNA的部分杂交，导致靶RNA的正常功能丧失。
• SYNTHESIS OF NOVEL 3′-DEOXY-3′-<i>C</i>-HYDROXYMETHYL NUCLEOSIDES WITH CONFORMATIONALLY RIGID SUGAR MOIETY AS POTENTIAL ANTIVIRAL AGENTS
  作者：Moon Woo Chun、Myung Jung Kim、Un Hee Jo、Joong Hyup Kim、Hee-Doo Kim、Lak Shin Jeong

  DOI：10.1081/ncn-100002354

  日期：2001.3.31

  Based on the fact that the ring expanded 3′-C-hydroxymethyl analogue of oxetanocin A exhibited potent antiviral activity, two types of conformationally rigid 3′-C-hydroxymethyl derivatives in which 2′-hydroxyl group is linked to the 4′-position or to the 6′-position were synthesized starting from 1,2;5,6-di-O-isopropylidene-D-glucose, respectively.

  基于氧杂环丁烷素A的扩环3'-C-羟甲基类似物表现出强大的抗病毒活性这一事实，将2'-羟基连接到4'-位置的两种构象刚性3'-C-羟甲基衍生物分别从1,2; 5,6-二-O-异亚丙基-D-葡萄糖开始合成或至6'-位。