3,5-dideoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose | 134056-14-7

• 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-dideoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: 3,5-dideoxy-3-[(benzyloxy)methyl]-1,2-O-isopropylidene-α-D-allofuranose；[(3aR,5R,6R,6aR)-5-(2-hydroxyethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 134056-14-7
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: VULPDHGYOBAUQM-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,5-dideoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose 在 4-二甲氨基吡啶 吡啶 、 偶氮二异丁腈 、 acidic cation-exchange resin (Dowex 50 W₈) 、 三正丁基氢锡 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.75h， 生成 (1R,5R,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane
  参考文献：
  名称：

  Building blocks for oligonucleotide analogs with dimethylene sulfide, sulfoxide, and sulfone groups replacing phosphodiester linkages

  摘要：

  Two routes are presented for the synthesis of 3',5'-bishomodeoxyribonucleosides, building blocks needed to synthesize oligodeoxynucleotide analogues where the OPO2O groups are replaced by CH2SCH2, CH2SOCH2, and CH2SO2CH2 units. Two of these have been coupled to create an uncharged analogue of a dinucleotide. As isosteric, achiral, and nonionic analogues of natural oligonucleotides stable to both enzymatic and chemical hydrolysis, such molecules have potential application as probes in the laboratory, in studies of the role of individual genes in biological function, and as ''antisense'' oligonucleotide analogues for the treatment of diseases.

  DOI：

  10.1021/jo00012a018
• 作为产物：
  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 4-二甲氨基吡啶 吡啶 、 dimethyl sulfide borane 、 硫酸 、 双氧水 、 碳酸氢钠 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 丁酮 为溶剂， 反应 151.0h， 生成 3,5-dideoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  Building blocks for oligonucleotide analogs with dimethylene sulfide, sulfoxide, and sulfone groups replacing phosphodiester linkages

  摘要：

  Two routes are presented for the synthesis of 3',5'-bishomodeoxyribonucleosides, building blocks needed to synthesize oligodeoxynucleotide analogues where the OPO2O groups are replaced by CH2SCH2, CH2SOCH2, and CH2SO2CH2 units. Two of these have been coupled to create an uncharged analogue of a dinucleotide. As isosteric, achiral, and nonionic analogues of natural oligonucleotides stable to both enzymatic and chemical hydrolysis, such molecules have potential application as probes in the laboratory, in studies of the role of individual genes in biological function, and as ''antisense'' oligonucleotide analogues for the treatment of diseases.

  DOI：

  10.1021/jo00012a018

文献信息

• Total Synthesis of 3‘,5‘-C-Branched Nucleosides
  作者：Eriks Rozners、Qun Xu

  DOI：10.1021/ol035619v

  日期：2003.10.1

  [reaction: see text] A novel total synthesis of 3',5'-C-branched uridine azido acid has been accomplished using stereoselective aldehyde alkynylation, Ireland-Claisen rearrangement, and iodolactonization as the key reactions. Compared to traditional routes that start from carbohydrates, the present methodology is more efficient, flexible for future optimization, and provides access to both enantiomers

  [反应：见正文]使用立体选择性醛烷基炔化，爱尔兰-克莱森重排和碘内酯化为关键反应，完成了3'，5'-C-支链尿苷叠氮酸的新型全合成。与从碳水化合物开始的传统路线相比，本方法更有效，更灵活，可用于将来的优化，并提供了产品的两种对映异构体的途径。因为关键化学反应不涉及3'-和5'-C取代基，所以我们的方法是3'，5'-C烷基核苷类似物的通用方法。
• HUANG, ZHEN;SCHNEIDER, K. CHRISTIAN;BENNER, STEVEN A., J. ORG. CHEM., 56,(1991) N, C. 3869-3882
  作者：HUANG, ZHEN、SCHNEIDER, K. CHRISTIAN、BENNER, STEVEN A.

  DOI：——

  日期：——