O³,O⁴-isopropylidene-O¹,O⁶-diphenyl-D-mannitol | 195833-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: O³,O⁴-isopropylidene-O¹,O⁶-diphenyl-D-mannitol
• 英文别名: O³,O⁴-Isopropyliden-O¹,O⁶-diphenyl-D-mannit；1,6-di-O-phenyl-3,4-O-isopropylidene-D-mannitol；(1R)-1-[(4R,5R)-5-[(1R)-1-hydroxy-2-phenoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenoxyethanol
• CAS: 195833-59-1
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: RPPJDDMTROQRAC-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O³,O⁴-isopropylidene-O¹,O⁶-diphenyl-D-mannitol 在 硫酸 作用下， 生成 O¹,O⁶-diphenyl-D-mannitol
  参考文献：
  名称：

  McSweeney et al., Journal of the Chemical Society, 1952, p. 37,40

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 、 苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到O³,O⁴-isopropylidene-O¹,O⁶-diphenyl-D-mannitol
  参考文献：
  名称：

  新型有效的C2对称性疟原虫I和II抑制剂。

  摘要：

  已经合成了一系列含有C（2）对称核心结构的疟疾纤溶酶（Plm）I和II抑制剂，并测试了其蛋白酶抑制活性。这些化合物可以使用涉及二环氧的酚亲核开环的直接合成来制备。合成的示例化合物对Plm I和II均显示出显着的抑制活性，尤其是15c，其K（i）值分别为2.7nM和0.25nM，并且对组织蛋白酶D的选择性超过100倍。

  DOI：

  10.1016/s0968-0896(02)00643-0

文献信息

• Silver(I) Oxide Mediated Highly Selective Monotosylation of Symmetrical Diols. Application to the Synthesis of Polysubstituted Cyclic Ethers
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1021/ol020071y

  日期：2002.7.1

  symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(I) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained

  [反应：见正文]在氧化银（I）和催化量的碘化钾存在下，对称二醇和低聚乙二醇与化学计量的对甲苯磺酰氯反应，选择性地导致单甲苯磺酸酯衍生物高产。在用过量的氧化银处理相应的二醇时，容易获得多取代的环醚。基于分子内氢键键合的两个羟基之间的酸度差异来解释高选择性。
• 1,2,5,6-Tetra- O -benzyl- d -mannitol derivatives as novel HIV protease inhibitors
  作者：Abderrahim Bouzide、Gilles Sauvé、Guy Sévigny、Jocelyn Yelle

  DOI：10.1016/s0960-894x(03)00677-2

  日期：2003.10

  The synthesis and structure-activity relationships of HIV protease inhibitors derived from carbohydrate alditols are discussed. We disclose a new series of 1,2,5,6-tetra-O-alkyl-D-mannitol exhibiting sub-micromolar activity against HIV-protease. This series of inhibitors are non-nitrogen containing HIV-protease inhibitors and they are readily prepared in a few chemical steps from inexpensive commercially

  讨论了衍生自碳水化合物糖醇的HIV蛋白酶抑制剂的合成与构效关系。我们公开了一个新的系列的1,2,5,6-四-O-烷基-D-甘露醇，对HIV蛋白酶表现出亚微摩尔活性。该系列抑制剂是不含氮的HIV蛋白酶抑制剂，它们可以在几个化学步骤中容易地由廉价的市售起始原料制备。
• Highly selective silver(I) oxide mediated monoprotection of symmetrical diols
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1016/s0040-4039(97)01328-2

  日期：1997.8

  Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.

  用Ag 2 O和烷基卤处理对称的二醇以良好至优异的产率得到单保护的衍生物。
• <i>C</i>₂-Symmetric Cyclic Selenium-Catalyzed Enantioselective Bromoaminocyclization
  作者：Feng Chen、Chong Kiat Tan、Ying-Yeung Yeung

  DOI：10.1021/ja311202e

  日期：2013.1.30

  A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and

  报道了使用 C(2)-对称甘露醇衍生的环状硒催化剂和化学计量的 N-溴邻苯二甲酰亚胺的三取代烯酰胺的催化不对称溴环化。得到的富含对映体的吡咯烷产物含有两个立体中心，可以进行重排以产生具有优异非对映选择性和对映体特异性的 2,3-二取代哌啶。
• Cyclic HIV-1 Protease Inhibitors Derived from Mannitol:  Synthesis, Inhibitory Potencies, and Computational Predictions of Binding Affinities
  作者：Johan Hultén、Nicholas M. Bonham、Ulrika Nillroth、Tomas Hansson、Guido Zuccarello、Abderrahim Bouzide、Johan Åqvist、Björn Classon、U. Helena Danielson、Anders Karlén、Ingemar Kvarnström、Bertil Samuelsson、Anders Hallberg

  DOI：10.1021/jm960728j

  日期：1997.3.1

  Ten C-2-symmetric cyclic urea and sulfamide derivatives have been synthesized from L-mannonic gamma-lactone and D-mannitol. The results of experimental measurement of their inhibitory potencies against HIV-1 protease were compared to calculated free energies of binding derived from molecular dynamics (MD) simulations. The compounds were selected, firstly, to enable elucidation of the role of stereochemistry for binding affinity (1a-d) and, secondly, to allow evaluation of the effects of variation in the link to the P1 and P1' phenyl groups on affinity (la and 2-5). Thirdly, compounds with hydrogen bond-accepting or -donating groups attached to the phenyl groups in the P2 and P2' side chains (6 and 7) were selected. Binding free energies were estimated by a linear response method, whose predictive power for estimating binding affinities from MD simulations was demonstrated.