6-O-benzyl-3-deoxy-3-N-(mesylamino)-4-O-mesyl-D-gulal | 850494-66-5

• 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-N-(mesylamino)-4-O-mesyl-D-gulal
• 英文别名: [(2R,3R,4S)-4-(methanesulfonamido)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl] methanesulfonate
• CAS: 850494-66-5
• 化学式: C₁₅H₂₁NO₇S₂
• 分子量: 391.466
• InChiKey: WRIFGKWZDVEZCH-RRFJBIMHSA-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-N-(mesylamino)-4-O-mesyl-D-gulal 在 potassium tert-butylate 作用下， 以 氘代苯 为溶剂， 反应 0.25h， 生成 (1S,2S,6S)-7-methylsulfonyl-2-(phenylmethoxymethyl)-3-oxa-7-azabicyclo[4.1.0]hept-4-ene
  参考文献：
  名称：

  Stereoselective Synthesis of 4-(N-Mesylamino)-2,3-unsaturated- α-O-glycosides via a New Glycal-Derived Vinyl α-N-(Mesyl)-aziridine

  摘要：

  N-Mesyl aziridine 7 alpha(1) a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of trans-NO-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7 alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N(mesylam ino)-2,3-unsaturated-aglycos ides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.

  DOI：

  10.1021/ol050053r
• 作为产物：
  描述：

  (1R,2R,6R)-2-Benzyloxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ene 在 吡啶 、 三苯基膦 、 N,N,N',N'-四甲基胍叠氮化物 作用下， 以 乙腈 为溶剂， 生成 6-O-benzyl-3-deoxy-3-N-(mesylamino)-4-O-mesyl-D-gulal
  参考文献：
  名称：

  d-Allal- and d-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles

  摘要：

  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.

  DOI：

  10.1055/s-0031-1291137

文献信息

• 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.
• 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.
• Stereoselective Synthesis of 4-(<i>N</i>-Mesylamino)-2,3-unsaturated- α-<i>O</i>-glycosides via a New Glycal-Derived Vinyl α<i>-N</i>-(Mesyl)-aziridine
  作者：Valeria Di Bussolo、Maria Rosaria Romano、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/ol050053r

  日期：2005.3.1

  N-Mesyl aziridine 7 alpha(1) a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of trans-NO-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7 alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N(mesylam ino)-2,3-unsaturated-aglycos ides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.
• 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.