3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 130469-40-8

• 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-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: 3-deoxy-3-<(benzoyloxy)methyl>-1:2,5:6-di-O-isopropylidene-α-D-allofuranose；3-deoxy-3-[(benzoyloxy)methyl]-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]methyl benzoate
• CAS: 130469-40-8
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: WTKWDWWYJPLNIS-XLKGFZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 吡啶 、 三甲基氯硅烷 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 acidic cation-exchange resin (Dowex 50 W₈) 、 硫酸 、 双氧水 、 三正丁基氢锡 、 碳酸氢钠 、 六甲基二硅氮烷 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 甲苯 、 丁酮 为溶剂， 反应 138.33h， 生成 N²-isobutyryl-7-<(2β,4R,5R)-4-<(benzoyloxy)methyl>-5-2-(hydroxyethyl)tetrahydrofuran-2-yl>guanine
  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 、 苯甲酰氯 在 4-二甲氨基吡啶 吡啶 作用下， 反应 23.0h， 生成 3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-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

• A ring-enlarged oxetanocin A analog as an inhibitor HIV infectivity
  作者：Christopher K. H. Tseng、Victor E. Marquez、George W. A. Milne、Ronald J. Wysocki、Hiroaki Mitsuya、Takuma Shirasaki、John S. Driscoll

  DOI：10.1021/jm00105a054

  日期：1991.1

  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.
• TSENG, CHRISTOPHER K. -H.;MARGUEZ, VICTOR E.;MILNE, GEORGE W. A.;WYSOCKI,+, J. MED. CHEM., 34,(1991) N, C. 343-349
  作者：TSENG, CHRISTOPHER K. -H.、MARGUEZ, VICTOR E.、MILNE, GEORGE W. A.、WYSOCKI,+

  DOI：——

  日期：——
• 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：——