[(2R,3S,4S,5R,6R)-6-[(4-bromophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate | 1196447-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,4S,5R,6R)-6-[(4-bromophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1196447-19-4
• 化学式: C₃₃H₄₈BrNO₉
• 分子量: 682.649
• InChiKey: CCSXAVVXSAPSTF-ZLOLNMDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 [(2R,3S,4S,5R,6R)-6-[(4-bromophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate 在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以91%的产率得到(S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(4-bromophenyl)-5,6-dehydropiperidin-4-one
  参考文献：
  名称：

  溴哌啶酮的立体选择性合成及其向环状杂环的转化

  摘要：

  脂肪族、芳香族和杂芳香族醛的 N-吡喃半乳糖基亚胺和 N-吡喃葡萄糖基亚胺与 1-甲氧基-3-三甲基甲硅烷氧基-1,3-丁二烯在多米诺曼尼希-迈克尔反应级联反应中反应，得到 2-取代的 5,6-脱氢-具有高非对映选择性的哌啶-4-酮。用 N-溴-琥珀酰亚胺处理这些环状烯胺酮产生相应的 2-取代 5-溴-5,6-脱氢哌啶酮，它们与 L-SelectrideⓇ 或甲基铜酸盐反应，得到具有高非对映选择性的饱和溴-哌啶酮。这些产物与硫代酰胺的缩合反应得到噻唑并哌啶 溴哌啶酮的立体选择性合成及其向环状杂环的转化

  DOI：

  10.1515/znb-2009-11-1251
• 作为产物：
  描述：

  2,3,4,6-四-O-叔戊酰基-beta-D-吡喃半乳糖胺 、 对溴苯甲醛 生成 [(2R,3S,4S,5R,6R)-6-[(4-bromophenyl)methylideneamino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  溴哌啶酮的立体选择性合成及其向环状杂环的转化

  摘要：

  脂肪族、芳香族和杂芳香族醛的 N-吡喃半乳糖基亚胺和 N-吡喃葡萄糖基亚胺与 1-甲氧基-3-三甲基甲硅烷氧基-1,3-丁二烯在多米诺曼尼希-迈克尔反应级联反应中反应，得到 2-取代的 5,6-脱氢-具有高非对映选择性的哌啶-4-酮。用 N-溴-琥珀酰亚胺处理这些环状烯胺酮产生相应的 2-取代 5-溴-5,6-脱氢哌啶酮，它们与 L-SelectrideⓇ 或甲基铜酸盐反应，得到具有高非对映选择性的饱和溴-哌啶酮。这些产物与硫代酰胺的缩合反应得到噻唑并哌啶 溴哌啶酮的立体选择性合成及其向环状杂环的转化

  DOI：

  10.1515/znb-2009-11-1251

文献信息

• Diastereoselective formation of aziridines from diazocarbonyl compounds and N-(O-pivaloylated d-galactosyl)benzylideneamines and ring-opening reactions with p-toluenethiol
  作者：Yizhou Zhao、Gang Wang、Shanshan Zhou、Zhongjun Li、Xiangbao Meng

  DOI：10.1039/c4ob00443d

  日期：——

  N-Galactosyl aziridines were synthesized via BF3·OEt2 promoted addition of carbenes generated from diazocarbonyl compounds with O-pivaloylated β-D-galactosylimines in good yields and high diastereoselectivity. The ring-opening reactions with p-toluenethiol of the aziridines provided enantiometrically pure β-S-substituted phenylalanine derivatives in a highly regioselective manner.

  N-半乳糖基氮丙啶是通过BF 3 ·OEt 2促进了重氮羰基化合物生成的卡宾与O-多酚基化的β- D-半乳糖苷的合成而合成的，具有高收率和高非对映选择性。与氮丙啶的对甲苯硫醇的开环反应以高度区域选择性的方式提供了对映体纯的β-S-取代的苯丙氨酸衍生物。
• Diastereoselective Povarov-Like Reaction Involving<i>O</i>-Pivaloylated<scp>D</scp>-Galactosylimine
  作者：Gang Wang、Boyu Li、Qinghua Lou、Zhongjun Li、Xiangbao Meng

  DOI：10.1002/adsc.201200761

  日期：2013.1.9

  A diastereoselective Povarov-like reaction using O-pivaloylated β-D-galactosylamine as the chiral auxiliary is described. The three-component reaction of chiral aldimines, cyclic enol ethers and nucleophiles afforded the desired products in good yields and high content of the main isomer. This procedure provides an efficient method to obtain multifunctional molecules carrying three contiguous chiral

  描述了使用O-吡咯烷基化的β-D-半乳糖胺作为手性助剂的非对映选择性的Povarov样反应。手性醛亚胺，环状烯醇醚和亲核试剂的三组分反应以良好的收率和高的主要异构体含量提供了所需的产物。该程序提供了一种高效的方法，可以以高立体选择性获得带有三个连续手性中心的多功能分子。
• Glycosylation-Induced and Lewis Acid-Catalyzed Asymmetric Synthesis of β-<i>N</i>-Glycosidically Linked α-Aminophosphonic Acids Derivatives
  作者：Yadan Wang、Fei Wang、Yangyun Wang、Zhiwei Miao、Ruyu Chen

  DOI：10.1002/adsc.200800406

  日期：2008.10.6

  The diastereospecific formation of β-N-glycosidically linked α-aminophosphonic acids derivatives has been achieved with high yield via a Mannich-type reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and boron trifluoride diethyl etherate as a catalyst in THF. Imines 3 of aromatic compounds and diethyl phosphite were converted to N-galactosyl α-aminoalkylphosphonate

  通过曼尼希型反应以高收率实现了β- N-糖苷键连接的α-氨基膦酸衍生物的非对映特异性形成。通过使用O-聚戊二酰化的半乳糖胺1作为手性模板并且使用三氟化硼二乙醚合硼酸酯作为催化剂在THF中进行反应。将芳族化合物和亚磷酸二乙酯的亚胺3转化为N-半乳糖基α-氨基烷基膦酸酯4，得到非对映异构体的比率高于19：1。该程序提供了对生物学上重要的半乳糖基α-氨基膦酸衍生物的快速访问。
• Highly efficient asymmetric vinylogous Mannich reaction induced by O-pivaloylated d-galactosylamine as the chiral auxiliary
  作者：Jipan Yu、Zhiwei Miao、Ruyu Chen

  DOI：10.1039/c0ob01048k

  日期：——

  The diastereospecific formation of β-N-glycoside-linked α-amino-2(5H)-furanone has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and ZnCl2·Et2O as a promoter in Et2O. Imines 3 of aromatic compounds and trimethylsiloxyfuran 4 were converted to N-galactosyl α-amino-2(5H)-furanone 5, giving ratios

  β- N-糖苷连接的α-氨基-2（5 H）-呋喃酮的非对映异构形成是通过乙烯基曼尼希反应以高收率实现的。将反应物通过使用执行ö -pivaloylated galactosylamine 1作为手性模板和氯化锌2 ·的Et 2 O作为在Et的启动子2 O.亚胺3的芳族化合物和trimethylsiloxyfuran的4转化成Ñ半乳糖苷α氨基-2-（ 5H）-呋喃酮5，非对映异构体的比率高于20：1。该程序可快速获取生物学上重要的γ-丁烯内酯衍生物。
• Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary
  作者：Haohao Yang、Bing Cui、Guiping Wu、Zhiwei Miao、Ruyu Chen

  DOI：10.1016/j.tet.2012.03.115

  日期：2012.6

  The diastereoselective formation of beta-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel-Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at -50 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.