6-O-benzyl-3-deoxy-3-amino-D-gulal | 850494-65-4

• 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-amino-D-gulal
• 英文别名: (2R,3R,4S)-4-amino-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol
• CAS: 850494-65-4
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: PXFCRLHMRXUCGP-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-O-benzyl-3-deoxy-3-amino-D-gulal 在 吡啶 、 tetrabutylammonium trimethylsilanolate 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 3-O-acetyl-1,5-anhydro-6-O-benzyl-2,4-dideoxy-4-(mesylamino)-D-arabino-hex-1-enitol
  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
• 作为产物：
  描述：

  (1R,2R,6R)-2-Benzyloxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ene 在 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-amino-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

• 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。
• 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.