(2R,2'R) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran | 154859-08-2

• 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: (2R,2'R) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran
• 英文别名: (2R)-2-phenyl-6-[(2R)-2-phenyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-2H-pyran
• CAS: 154859-08-2
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: SLYXNDLMNCRUQO-WOJBJXKFSA-N

物化性质

• 沸点：
  469.0±45.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,2'R) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran 在 双(乙腈)氯化钯(II) 、 正丁基锂 、 camphor-10-sulfonic acid 、 三丁基氯化锡 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 (-)-diisopinocamphenylborane chloride 、 calcium chloride 、 copper dichloride 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 58.0h， 生成 (2'S,2''S,6'S,6''S) 2-O,5-O-dibenzoyl-1-O,6-O-(6,6'-diphenyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-D-myo-inositol
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j
• 作为产物：
  描述：

  (2RS,6R) 2-benzenesulfonyl-6-phenyltetrahydropyran 在 双(乙腈)氯化钯(II) 、 正丁基锂 、 三丁基氯化锡 、 N,N-二异丙基乙胺 、 copper dichloride 作用下， 生成 (2R,2'R) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran 、 meso-2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'-bi-2H-pyran
  参考文献：
  名称：

  Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.

  摘要：

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.

  DOI：

  10.1016/0957-4166(95)00318-j

文献信息

• Design and Synthesis of New Aminoglycoside Antibiotics Containing Neamine as an Optimal Core Structure:  Correlation of Antibiotic Activity with in Vitro Inhibition of Translation
  作者：William A. Greenberg、E. Scott Priestley、Pamela S. Sears、Phil B. Alper、Christoph Rosenbohm、Martin Hendrix、Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1021/ja9910356

  日期：1999.7.1

  The structure and activity of the pseudodisaccharide core found in aminoglycoside antibiotics was probed with a series of synthetic analogues in which the position of amino groups was varied around the glucopyranose ring. The naturally occurring structure neamine was the best in the series according to assays for in vitro RNA binding and antibiotic activity. With this result in hand, neamine was used

  在氨基糖苷类抗生素中发现的假二糖核心的结构和活性是用一系列合成类似物探测的，其中氨基的位置在吡喃葡萄糖环周围发生变化。根据体外 RNA 结合和抗生素活性的测定，天然存在的结构 neamine 是该系列中最好的。有了这个结果，neamine 被用作合成新抗生素的共同核心结构，评估其与大肠杆菌 16S A 位点核糖体 RNA 模型的结合、体外蛋白质合成抑制和抗生素活性。RNA结合的分析揭示了RNA结合的相对亲和力和特异性与抗菌功效之间的一些相关性。然而，相关性不是线性的。这一结果促使我们开发了体外翻译试验，以更好地了解氨基糖苷类-RNA 的相互作用。体外翻译抑制与抗生素活性之间的线性相关性...
• Synthesis, Characterization and Reactions of Enantiomerically Pure ‘Winged’ Spirane Porphyrazines
  作者：Shun-ichiro Hachiya、Andrew S. Cook、D.Bradley G. Williams、Antonio Garrido Montalban、Anthony G.M. Barrett、Brian M. Hoffman

  DOI：10.1016/s0040-4020(00)00607-4

  日期：2000.8

  A series of enantiomerically pure porphyrazineoctaol derivatives have been prepared from l-(+)-dimethyl tartrate via conversion into the corresponding dispoke protected dihydroxymaleonitrile, Linstead macrocyclization and transmetallation. The derived chloromanganese(III) complexes catalyzed the epoxidation of styrene with sodium hypochlorite as the oxygen atom source but with modest enantioselectivities

  从1-（+）-酒石酸二甲酯通过转化成相应的受保护的二羟基马来腈，Linstead大环化和金属转移反应，制备了一系列对映体纯的卟啉嗪辛醇衍生物。衍生的氯锰（III）络合物以次氯酸钠作为氧原子源催化苯乙烯的环氧化，但对映选择性不高（<25％）。
• Dispiroketals in synthesis (part 9): Resolution of 1,2-diols using a C2-symmetric diphenyltetrahydrobipyran.
  作者：Paul J. Edwards、David A. Entwistle、Steven V. Ley、Dafydd R. Owen、Emily J. Perry

  DOI：10.1016/0957-4166(94)80016-2

  日期：1994.4

  A series of 1,2-diols were resolved by the enantioselective formation of the thermodynamically most stable dispiroketal using (2R,2'R) and (2S,2'S) 2,2'-diphenyl-3,3',4,4'-tetrahydro-6,6'- 2 and 3. Deprotection was achieved using a metal ammonia reduction to liberate the resolved diols.
• Dispiroketals in synthesis (Part 17): Regioselective protection of D-glucopyranoside D-galactopyranoside and D-mannopyranoside substrates.
  作者：Paul J. Edwards、David A. Entwistle、Christophe Genicot、Steven V. Ley、Giuseppina Visentin

  DOI：10.1016/s0957-4166(00)80404-8

  日期：1994.12

  Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] hexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.
• Dispiroketals in synthesis (part 8): Regioselective protection of D-glucopyranose substrates
  作者：David A. Entwistle、Andrew B. Hughes、Steven V. Ley、Giuseppina Visentin

  DOI：10.1016/s0040-4039(00)75815-1

  日期：1994.1

  A new process for the efficient regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4]hexadecanes (dispiroketals) of various D-elucopyranosyl substrates by the chiral recognition of enantiomeric trans 1,2-diol relationships is described. This was achieved using the novel enantiomerically pure 2,2'-disubstituted 3,3',4,4'-tetrahydro-6,6'-bi-2H-pyrans 1, 2 and 11. New conditions for the removal of dispiroketal protecting groups are presented.