(2R,4S,5R)-2-methyl-4-(trityloxymethyl)-1,3-dioxan-5-ol | 95870-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,4S,5R)-2-methyl-4-(trityloxymethyl)-1,3-dioxan-5-ol
• 英文别名: 2,4-O-Ethyliden-1-O-trityl-D-threit
• CAS: 95870-62-5
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: BPXDANWMPNDKPK-FOVJLYNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-2-methyl-4-(trityloxymethyl)-1,3-dioxan-5-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 乙醚 为溶剂， 反应 5.33h， 生成 (2R,4R,5R)-5-Ethyl-4-hydroxymethyl-2-methyl-[1,3]dioxan-5-ol
  参考文献：
  名称：

  Diastereoselectivity of the reactions of organometallic reagents with protected d- and l-erythrulose 1,3-O-ethylidene acetals

  摘要：

  1,3-O-Ethylidene acetals of D- and L-erythrulose bearing various protecting groups on the 4-OH group have been prepared using D-glucose as the starting material. The stereo-selectivity of the additions of several organometallic reagents to the carbonyl group of these compounds has then been investigated. In contrast to previously studied erythrulose derivatives, the type of protecting group does not play a significant role in the stereocontrol of the process. Theoretical calculations have been performed in order to find an explanation of this behaviour. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00540-x
• 作为产物：
  描述：

  1,3-O-Ethylidene-L-erythritol 、 三苯基氯甲烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到(2R,4S,5R)-2-methyl-4-(trityloxymethyl)-1,3-dioxan-5-ol
  参考文献：
  名称：

  Diastereoselectivity of the reactions of organometallic reagents with protected d- and l-erythrulose 1,3-O-ethylidene acetals

  摘要：

  1,3-O-Ethylidene acetals of D- and L-erythrulose bearing various protecting groups on the 4-OH group have been prepared using D-glucose as the starting material. The stereo-selectivity of the additions of several organometallic reagents to the carbonyl group of these compounds has then been investigated. In contrast to previously studied erythrulose derivatives, the type of protecting group does not play a significant role in the stereocontrol of the process. Theoretical calculations have been performed in order to find an explanation of this behaviour. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00540-x

文献信息

• Stereochemistry of the [2+2] Cycloaddition of Chlorosulfonyl Isocyanate to Chiral Alkoxyallenes Derived from 1,3-Alkylidene-L-erythritol and -D-threitol
  作者：Tong�Thanh Danh、Wojciech Bocian、Lech Kozerski、Patrycja Szczukiewicz、Jadwiga Frelek、Marek Chmielewski

  DOI：10.1002/ejoc.200400557

  日期：2005.1

  The [2+2] cycloaddition of chlorosulfonyl isocyanate to alkoxyallenes derived from ethylidene and benzylidene erythritols and threitols proceeds with a moderate asymmetric induction in the case of the erythritols and with a very low induction in the case of threitols. This indicates that the erythritol derivatives may exist in solution in one predominant conformation while the threitol derivatives

  氯磺酰基异氰酸酯与衍生自亚乙基和亚苄基赤藓糖醇和苏糖醇的烷氧基丙二烯的 [2+2] 环加成在赤藓糖醇的情况下以适度的不对称诱导进行，在苏糖醇的情况下以非常低的诱导进行。这表明赤藓糖醇衍生物可能以一种主要构象存在于溶液中，而苏糖醇衍生物表现为一种构象集合。烷氧基丙二烯的构象通过各种 NMR 技术以及从头计算进行研究。由此获得的结果与我们基于环加成立体选择性的预测完全一致。通过环加成获得的氮杂环丁酮在氮原子处进行分子内烷基化以提供相应的三环头孢菌素。所得氮杂环丁酮和头孢菌素的绝对构型使用 NMR 和 CD 光谱进行分配。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Diastereoselectivity of the reactions of organometallic reagents with protected d- and l-erythrulose 1,3-O-ethylidene acetals
  作者：M. Carda、P. Casabó、F. González、S. Rodríguez、L.R. Domingo、J.A. Marco

  DOI：10.1016/s0957-4166(96)00540-x

  日期：1997.2

  1,3-O-Ethylidene acetals of D- and L-erythrulose bearing various protecting groups on the 4-OH group have been prepared using D-glucose as the starting material. The stereo-selectivity of the additions of several organometallic reagents to the carbonyl group of these compounds has then been investigated. In contrast to previously studied erythrulose derivatives, the type of protecting group does not play a significant role in the stereocontrol of the process. Theoretical calculations have been performed in order to find an explanation of this behaviour. (C) 1997 Elsevier Science Ltd.