(2R,4S,5R)-4-Benzyloxymethyl-2,5-dimethyl-[1,3]dioxan-5-ol | 188925-29-3

• 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: (2R,4S,5R)-4-Benzyloxymethyl-2,5-dimethyl-[1,3]dioxan-5-ol
• 英文别名: (2R,4S,5R)-2,5-dimethyl-4-(phenylmethoxymethyl)-1,3-dioxan-5-ol
• CAS: 188925-29-3
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: MXCJLVNLTRVFOI-KWCYVHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-4-Benzyloxymethyl-2,5-dimethyl-[1,3]dioxan-5-ol 在 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 1,2-乙二硫醇 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 (2R,3S)-1,3,4-tri-O-benzyl-2-methylbutane-1,2,3,4-tetraol
  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 在 4-二甲氨基吡啶 、 草酰氯 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.33h， 生成 (2R,4S,5R)-4-Benzyloxymethyl-2,5-dimethyl-[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

• 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.