(2R,3R)-2,4-bis(benzyloxy)butane-1,3-diol | 1373934-32-7

• 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,3R)-2,4-bis(benzyloxy)butane-1,3-diol
• 英文别名: (2R,3R)-2,4-bis(phenylmethoxy)butane-1,3-diol
• CAS: 1373934-32-7
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: DHSYDAKMRZRYEE-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,4-bis(benzyloxy)butane-1,3-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到(4R,5R)-5-(benzyloxy)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  An efficient synthesis of the polar part of sulfamisterin and its analogs

  摘要：

  An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.019
• 作为产物：
  描述：

  (2S,3R)-2,4-bis(benzyloxy)-3-hydroxybutanal 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以17.6 mg的产率得到(2R,3R)-2,4-bis(benzyloxy)butane-1,3-diol
  参考文献：
  名称：

  An efficient synthesis of the polar part of sulfamisterin and its analogs

  摘要：

  An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.019

文献信息

• Chiral Primary−Tertiary Diamine−Brønsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes
  作者：Jiuyuan Li、Niankai Fu、Xin Li、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1021/jo100976e

  日期：2010.7.2

  Highly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary−tertiary diamine−Brønsted acid salts are found to promote the cross-aldol reactions of aldehydes with high activity and syn selectivity. Among various vicinal diamines screened, l-phenylalanine derived

  在氨基催化领域，醛的高度顺-选择性交叉-羟醛反应一直是具有挑战性的主题。为了达到这个目的，已经研究了手性伯胺，发现伯叔叔二胺布朗斯台德酸盐可以高活性和顺选择性地促进醛的交叉羟醛反应。在筛选的各种邻位二胺中，1-苯丙氨酸衍生的2a / TfOH共轭物被确定为最佳催化剂，显示出良好的催化活性（高达97％的产率）和高的合成选择性（syn / anti高达24：1、87％ee） 。当前的催化选择性地与较小的脂族醛供体（例如丙醛和异丁醛）一起起作用，但不适用于带有较大β-取代基（> Me）的脂族醛。另外，使用2a / TfOH共轭物也使糖醛供体的第一个顺-选择性交叉-羟醛反应成为可能。