(2S)-2-phenyl-6-[(2S)-2-phenyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-2H-pyran | 154859-09-3

• 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: (2S)-2-phenyl-6-[(2S)-2-phenyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-2H-pyran
• CAS: 154859-09-3
• 化学式: C₂₂H₂₂O₂
• 分子量: 318.415
• InChiKey: SLYXNDLMNCRUQO-PMACEKPBSA-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：

  (2S)-2-phenyl-6-[(2S)-2-phenyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-2H-pyran 在 sodium hydroxide 、 camphor-10-sulfonic acid 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2'S,2''S,6'S,6''S) 1-O,6-O-(6,6'-diphenyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-2-O,3-O,4-O,5-O-tetrabenzyl-D-myo-inositol
  参考文献：
  名称：

  在合成Dispiroketals（部分11）：伴随对映选择性和2,5-二苯甲酰基的区域选择性保护肌醇肌醇

  摘要：

  2,5-二苯甲酰基肌肌醇，对称的多元醇，可以是对映选择性地同时和区域选择性使用手性的二烯烃（保护1），（2）和（3）。脱保护，以得到d或L-1,6-四ö苄基肌-肌醇（8）和（12）分别被实现了使用三氟乙酸。

  DOI：

  10.1016/0040-4039(94)85337-1
• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 双(乙腈)氯化钯(II) 、 正丁基锂 、 dimethyl sulfide borane 、 4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene 、 三丁基氯化锡 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 calcium chloride 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 (2S)-2-phenyl-6-[(2S)-2-phenyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-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

• Dispiroketals in synthesis. Part 23.1 A new route to (+)-D-conduritol B from myo-inositol
  作者：Jean E. Innes、Paul J. Edwards、Steven V. Ley

  DOI：10.1039/a700422b

  日期：——

  Using (2S,2′S)-2,2′-diphenyl-6,6′-bi(3,4-dihydro-2 H-pyran) to effect a simultaneous protection–resolution of a myo-inositol derivative, a new synthesis of (+)-D-conduritol B has been achieved.

  使用(2S,2′S)-2,2′-二苯基-6,6′-双(3,4-二氢-2H-吡喃)对肌醇衍生物进行同时保护与拆分，已经实现了(+)-D-康杜醇B的新合成。
• Ley, Steven V.; Humphries, Alexander C.; Eick, Holger, Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3907 - 3911
  作者：Ley, Steven V.、Humphries, Alexander C.、Eick, Holger、Downham, Robert、Ross, Andrew R.、Boyce, Richard J.、Pavey, John B. J.、Pietruszka, Joerg

  DOI：——

  日期：——
• 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.