6-O-benzyl-3-deoxy-3-(mesylamino)-4-O-mesyl-D-glucal | 878800-62-5

• 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: 6-O-benzyl-3-deoxy-3-(mesylamino)-4-O-mesyl-D-glucal
• 英文别名: [(2R,3S,4R)-4-(methanesulfonamido)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl] methanesulfonate
• CAS: 878800-62-5
• 化学式: C₁₅H₂₁NO₇S₂
• 分子量: 391.466
• InChiKey: WRIFGKWZDVEZCH-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-3-deoxy-3-(mesylamino)-4-O-mesyl-D-glucal 在 tetrabutylammonium trimethylsilanolate 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以67%的产率得到6-O-benzyl-4-deoxy-4-(mesylamino)-D-gulal
  参考文献：
  名称：

  Stereoselective Uncatalyzed Synthesis of 2,3-Unsaturated-4-N-substituted-β-O-glycosides by Means of a New d-Galactal-Derived N-(Mesyl)-aziridine

  摘要：

  The reaction of the new (D)-galactal-derived allylic aziridine 1 beta with O-nucleophiles (alcohols and monosaccharides) affords, in a high to complete beta-stereoselectivity, the corresponding 2,3-unsaturated-beta-O-glycosides bearing a beta-N-functionality at C(4).

  DOI：

  10.1021/jo051877p
• 作为产物：
  描述：

  4-O-mesyl-6-O-benzyl-D-gulal 在 吡啶 、 potassium tert-butylate 、 苯硫酚 、 三乙胺 、 tetramethylguanidinum azide 、 tin(ll) chloride 作用下， 以 乙腈 为溶剂， 反应 7.83h， 生成 6-O-benzyl-3-deoxy-3-(mesylamino)-4-O-mesyl-D-glucal
  参考文献：
  名称：

  Stereoselective Uncatalyzed Synthesis of 2,3-Unsaturated-4-N-substituted-β-O-glycosides by Means of a New d-Galactal-Derived N-(Mesyl)-aziridine

  摘要：

  The reaction of the new (D)-galactal-derived allylic aziridine 1 beta with O-nucleophiles (alcohols and monosaccharides) affords, in a high to complete beta-stereoselectivity, the corresponding 2,3-unsaturated-beta-O-glycosides bearing a beta-N-functionality at C(4).

  DOI：

  10.1021/jo051877p

文献信息

• N-Nosyl as a stereoselectivity-improving and easily removable group in the O-glycosylation of d-allal and d-galactal-derived allyl aziridines. Stereospecific synthesis of 4-amino-2,3-unsaturated-O-glycosides
  作者：Valeria Di Bussolo、Maria Rosaria Romano、Mauro Pineschi、Paolo Crotti

  DOI：10.1016/j.tet.2006.12.069

  日期：2007.3

  The glycosylation of alcohols, phenol, and partially protected monosaccharides with the diastereoisomeric d-allal and d-galactal-derived N-nosyl aziridines 2α and 2β leads to the corresponding 4-N-(nosylamino)-2,3-unsaturated-α-O- (6α) and β-O-glycosides and disaccharides (6β), respectively, in a stereospecific substrate-dependent O-glycosylation process. The N-(nosylamino) group of 6α and 6β can easily

  醇，苯酚和部分受保护的单糖与非对映异构体的d- allal和d-galactal衍生的N - nosyl氮丙啶2α和2β的糖基化反应会导致相应的4- N-（nosylamino）-2,3-unsaturated-α- O-（6α）和β- O-糖苷和二糖（6β）分别在立体特异性底物依赖性O-糖基化过程中产生。6α和6β的N-（nosylamino）基团 可以很容易地脱保护，得到相应的4-氨基-2,3-不饱和-O-糖苷7α和7β，对我们的糖基化方案具有更高的价值。
• Enantiopure <i>Cis</i>-2,5-Disubstituted 2,5-Dihydropyrroles from <scp>d</scp>-Glycal-Derived Vinyl Aziridines
  作者：Valeria Di Bussolo、Ileana Frau、Stefano Crotti、Gloria Uccello-Barretta、Federica Balzano、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/ol402927s

  日期：2013.12.6

  Upon treatment with the K- and Li-enolates of a methylene active compound, such as dimethyl malonate and dibenzoylmethane, D-allal- and c-galactal-derived vinyl N-mesyl aziridines are stereoselectively transformed, in a unique step, into diastereoisomeric, highly functionalized, enantiopure cis-2,5-disubstituted N-mesyl-2,5-dihydropyrroles.
• d-Allal- and d-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles
  作者：Valeria Di Bussolo、Paolo Crotti、Ileana Frau、Mauro Pineschi

  DOI：10.1055/s-0031-1291137

  日期：——

  The regioselectivity and stereoselectivity were examined of the addition reactions of O-, C-, N-and S-nucleophiles to D-allal- and D-galactal-derived N-mesylaziridines. The ratio of 1,4-regioselectivity (exclusive syn-1,4-addition) to 1,2-regioselectivity (exclusive anti-1,2-addition) was strictly and directly dependent on the ability of the nucleophile to coordinate with the nitrogen atom of the aziridine.
• Aminolysis of glycal-derived allyl epoxides and activated aziridines. Effects of the absence of coordination processes on the regio- and stereoselectivity
  作者：Valeria Di Bussolo、Lorenzo Checchia、Maria Rosaria Romano、Lucilla Favero、Mauro Pineschi、Paolo Crotti

  DOI：10.1016/j.tet.2009.11.059

  日期：2010.1

  The addition of primary and secondary aliphatic amines to glycal-derived allyl epoxides is completely 1,2-regio- and anti-stereoselective, whereas mixtures of the corresponding anti-1,2- [3-N-(substituted-amino) glycals] and anti-1,4-addition products (N-glycosyl amines) are obtained with N-(mesyl)-aziridines. In this way, structural moieties, otherwise difficult to synthesize, are obtained by means of a very simple protocol. The regio- and stereoselectivity observed with epoxides is the consequence of an isomerization process, whereas the result obtained with aziridines is explained by the absence of an effective substrate-nucleophile (amine) coordination. (C) 2009 Elsevier Ltd. All rights reserved.