phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-mannopyranoside | 150809-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-mannopyranoside
• 英文别名: Phenyl 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-seleno-α-D-mannopyranoside；(2R,3S,4R,5S,6R)-5-azido-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylselanyloxane
• CAS: 150809-71-5
• 化学式: C₃₃H₃₃N₃O₄Se
• 分子量: 614.603
• InChiKey: XBLAAOVLJTTYST-CVCQUZQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-mannopyranoside 在 吡啶 、 1,3-丙二硫醇 、 sodium tetrahydroborate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 3 A molecular sieve 、 mercury(II) trifluoroacetate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 5.5h， 生成 2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-D-葡萄糖酸-1,5-内酯
  参考文献：
  名称：

  Convenient Preparation of Perbenzylated 2-Azido and 2-N-Acetylamino-2-Deoxy-d-Hexono-1,5-Lactones by Oxidation of the Corresponding Lactols

  摘要：

  2-Azido-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (1, 2, 3) were oxidized with DMSO in the presence of acetic anhydride. From 1 and 2 the corresponding lactone derivatives were obtained in good yield (89-92%), whereas from 3, glucono-1,5-lactone was obtained (92%) after complete epimerization at C-2. 2-N-Acetylamino-3,4,6-tri-O-benzyl-2-deoxy-D-galacto, gluco and mannopyranoses (7, 8, 9) were obtained from the corresponding 2-azido phenylselenoglycopyranosides (13, 14, 15) by reduction, N-acetylation and hydrolysis catalyzed by mercury trifluoroacetate. Oxidation of 7 and 8 by tetra-n-propylammonium tetra-oxoruthenate (VII) in the presence of 4-methylmorpholine-N-oxide afforded the corresponding lactones in good yield (90%) and high purity. Epimerization at C-2 occurred during oxidation of 9 and perbenzylated D-glucono-1,5-lactone (11) was obtained (90%).

  DOI：

  10.1080/07328309608005438
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 3,4,6-三苄氧基-D-葡萄烯糖 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-mannopyranoside 、 phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside
  参考文献：
  名称：

  从糖基中制备多种保护的 2-azido-2-deoxyglycopyranoses

  摘要：

  描述了从相应的糖类中制备出多种保护的 2-azido-2-deoxyglycopyranosides 的新的和有效的方法。糖基首先通过叠氮基-苯基硒基化作用转化为受保护的苯基 2-叠氮基-2-脱氧-硒基糖苷。根据存在的保护基团采用两种方法：在（二乙酰氧基碘）苯存在下制备全乙酰化糖醛（方法 A）或叠氮化三甲基甲硅烷和四正丁基氟化铵在 N-苯基硒代邻苯二甲酰亚胺用于过苄基化糖类（程序 B）。葡萄糖-甘露糖混合物 (90%) 从受保护的 d-glucal 中获得，而只有半乳糖异构体由受保护的 d-半乳醛 (75%) 形成。用 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和 1,5-anhydro-2-deoxy-3,4-O-isopropylidene-d-lyxo-hex-l-enitol 和其 6-0-乙酰基 I、6-0-烯丙基、6-0-苄基和

  DOI：

  10.1139/v95-046

文献信息

• New and efficient synthesis of protected 2-azido-2-deoxy-glycopyranoses from the corresponding glycal
  作者：Stanislas Czernecki、Ebtissam Ayadi、Dominique Randriamandimby

  DOI：10.1039/c39940000035

  日期：——

  Diversely protected 2-azido-2-deoxy-D-glycopyranoses are prepared by azido phenylselenylation of the corresponding glycal followed by hydrolysis of the resulting selenoglycosides: from protected D-galactal, protected 2-azido-2-deoxy-D-galactopyranose is obtained, as the sole product in 72% overall yield.

  通过将相应的糖醛基进行叠氮苯基硒化，然后水解得到的硒代糖苷，可以制备出受保护的2-叠氮-2-脱氧-D-吡喃糖：从受保护的D-半乳糖醛中可以得到受保护的2-叠氮-2-脱氧-D-吡喃糖，作为唯一产物，总产率为72%。
• Azido-phenylselenylation of protected glycals
  作者：Stanislas Czernecki、Dominique Randriamandimby

  DOI：10.1016/s0040-4039(00)61509-5

  日期：1993.12

  Anti-Markovnikov azido-phenylselenylation of diversely protected glycals affords protected phenyl 2-azido-2-deoxy-α-selenoglycopyranosides. From D-glucal, the α-manno and α-gluco isomers are obtained, whereas from D-galactal, a complete stereocontrol is observed, affording exclusively the α-galacto isomer in 70% yield.

  各种保护的糖类的反马尔科夫尼科夫叠氮基-苯基硒基化可提供受保护的苯基2-叠氮基-2-脱氧-α-硒基糖吡喃糖苷。从d -glucal，得到α -甘露和α葡糖异构体，而来自d -galactal，观察到完整的立体控制，得到只在70％的产率α半乳异构体。
• Homogeneous azidophenylselenylation of glucals
  作者：Yuri V. Mironov、Andrei A. Sherman、Nikolay E. Nifantiev

  DOI：10.1016/j.mencom.2008.09.003

  日期：2008.9

  The homogeneous azidophenylselenylation of diversely protected mono-, di- and trisaccharide glucals was studied to evaluate the influence of protective groups, N-3 and I donors, temperature and solvent on the stereoselectivity of the formation of corresponding phenyl 2-azido-2-deoxy-1-seleno-alpha-D-gluco- and -manno-adducts.
• Synthesis of phenyl 2-azido-2-deoxy-1-selenoglycosides from glycals
  作者：F. Santoyo-Gonzalez、F. G. Calvo-Flores、P. Garcia-Mendoza、F. Hernandez-Mateo、J. Isac-Garcia、R. Robles-Diaz

  DOI：10.1021/jo00074a048

  日期：1993.10