(2S,3S)-4-azido-2,3-O-isopropylidene-1,2,3-butanetriol | 84252-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-4-azido-2,3-O-isopropylidene-1,2,3-butanetriol
• 英文别名: (2S,3S)-4-azido-2,3-O-isopropylidenebutane-1,2,3-triol；4-azido-4-deoxy-2,3-O-isopropylidene-L-threitol；((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol；[(4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 84252-35-7
• 化学式: C₇H₁₃N₃O₃
• 分子量: 187.199
• InChiKey: YGMHEVVRKCWTNX-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-4-azido-2,3-O-isopropylidene-1,2,3-butanetriol 在 potassium carbonate 、 sodium amide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 12.75h， 生成 methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propiolate
  参考文献：
  名称：

  Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

  摘要：

  The intramolecular alkyne-azide Huisgen [3+2] cycloaddition reaction as a 'click-chemistry' reaction without a metal catalyst has been studied under aerobic conditions. The synthesis of various pyrrolidine-triazole hybrid compounds has also been achieved by using this intramolecular cycloaddition reaction in water with complete 1,5-regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.011
• 作为产物：
  描述：

  (4R,5R)-4,5-二乙氧基羰基-2,2-二甲基二氧 在 lithium aluminium tetrahydride 、 sodium azide 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S)-4-azido-2,3-O-isopropylidene-1,2,3-butanetriol
  参考文献：
  名称：

  Retracted Article: Synthesis of diacylglycerol analogs bearing photoaffinity tags for labelling mammalian diacylglycerol kinase

  摘要：

  这份通讯报告了合成带有不同光亲和标记的二酰基甘油（DAG）探针，以进行交联并减少二酰基甘油激酶（DGK）的活性。

  DOI：

  10.1039/c4ra16730a

文献信息

• Chiral 4-(Diphenylphosphanyl)-1-(dialkylamino)butane Ligands – Synthesis, Applications in Asymmetric Alkylation and Theoretical Study
  作者：Fabien Robert、Françoise Delbecq、Christelle Nguefack、Denis Sinou

  DOI：10.1002/(sici)1099-0682(200002)2000:2<351::aid-ejic351>3.0.co;2-q

  日期：2000.2

  3-O-isopropylidene-D-threitol. These ligands, associated with Pd2(dba)3, gave enantioselectivities of up to 75% in the alkylation of racemic 1,3-diphenylprop-2-enyl acetate with dimethyl malonate anion. A theoretical study shows the important role played by two factors in the alkylation reaction: steric control, leading to the formation of a unique diastereoisomer of the π-allylpalladium complex, and orbital control

  各种 4-(二苯基膦基)-1-(二烷基氨基) 丁烷配体由商业 (2S,3S)-2,3-O-异亚丙基-D-苏糖醇制备。这些与 Pd2(dba)3 相关的配体在外消旋 1,3-二苯基丙-2-烯基乙酸酯与丙二酸二甲酯阴离子的烷基化反应中具有高达 75% 的对映选择性。一项理论研究表明，两个因素在烷基化反应中起着重要作用：空间控制，导致形成独特的 π-烯丙基钯配合物的非对映异构体，以及轨道控制，将亲核试剂的攻击定向到磷原子.
• Enantiomerically pure 4-amino-1,2,3-trihydroxybutylphosphonic acids
  作者：Andrzej E. Wróblewski、Iwona E. Głowacka

  DOI：10.1016/j.tet.2005.09.057

  日期：2005.12

  (1S,2R,3S)-, (1R,2R,3S)- and (1S,2R,3R)-4-amino-1,2,3-trihydroxybutylphosphonic acids were synthesised. The synthetic strategy involved preparation of the respective 4-azido-2,3-O-isopropylidene-L-threose or -D-erythrose, addition of dialkyl phosphites, separation of C-1 epimeric O,O-dibenzyl phosphonates, the reduction of azides and the removal of the protecting groups. The (2R,3S) and (2R,3R) configurations in the final products were secured by employing diethyl L-tartrate and D-isoascorbic acid as starting materials. The stereochemical course of the addition to the carbonyl groups in 4-azido-2,3-O-isopropylidene-L-threose or -D-erythrose followed that established earlier for 2,3-0-isopropylidene-D-glyceraldehyde and similar (3:1-4:1) diastereoselectivities were achieved. (c) 2005 Elsevier Ltd. All rights reserved.

  （1S,2R,3S)-、(1R,2R,3S)-和（1S,2R,3R)-4-氨基-1,2,3-三羟基丁基膦酸被成功合成。该合成策略包括以下步骤：制备相应的4-叠氮-2,3-O-异丙叉基-L-苏 sugar或-D-赤 sugar，添加二烷基次磷酸酯，分离C-1异构体O,O-二苯甲基膦酸酯，还原叠氮基团以及去除保护基团。最终产物中的（2R,3S）和（2R,3R）构型通过使用乙酸-D-异抗坏血酸和(D)-异抗坏血酸作为起始材料来实现。在4-叠氮-2,3-O-异丙叉基-L-苏糖或-D-赤糖的羰基加成过程中，其立体化学路径遵循先前为2,3-O-异丙叉基-D-甘油醛等化合物建立的模式，实现了类似的（3:1-4:1）对映选择性。（C）2005 Elsevier Ltd. 保留所有权利。 注：上述化合物的中文命名可能不完全标准，实际应用中应参考相关化学命名规则和文献。
• AMPHIPHILIC COMPOUNDS AND SELF-ASSEMBLING COMPOSITIONS MADE THEREFROM
  申请人：Ladet Sébastien

  公开号：US20120052042A1

  公开（公告）日：2012-03-01

  The present disclosure relates to amphiphilic compounds, self assembling compositions formed from the amphiphilic compounds and methods of making such compositions.

  本公开涉及两性化合物、由两性化合物形成的自组装组合物以及制备这种组合物的方法。
• Compounds and medical devices activated with solvophobic linkers
  申请人：Sofradim Production

  公开号：US10632207B2

  公开（公告）日：2020-04-28

  The present disclosure relates to compounds and medical devices activated with a solvophobic material functionalized with a first reactive member and methods of making such compounds and devices.

  本公开涉及用第一反应物官能化的疏溶材料激活的化合物和医疗设备，以及制造这种化合物和设备的方法。
• Synthesis of hybrid 1,2,3-triazolo-δ-lactams/lactones using Huisgen [3+2] cycloaddition ‘click-chemistry’ in water
  作者：Indresh Kumar、Sravendra Rana、Jae Whan Cho、Chandrashekhar V. Rode

  DOI：10.1016/j.tetasy.2010.02.002

  日期：2010.3

  The synthesis of a new class of hybrid 1,2,3-triazozlo-delta-lactams/lactones has been achieved using the Huisgen [3+2] dipolar cycloaddition 'click-chemistry' reaction of various organic azides with an activated alkyne in water, followed by cyclization. (C) 2010 Elsevier Ltd. All rights reserved.