phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside | 150809-70-4

• 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-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-5-azido-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylselanyloxane
• CAS: 150809-70-4
• 化学式: C₃₃H₃₃N₃O₄Se
• 分子量: 614.603
• InChiKey: XBLAAOVLJTTYST-YKNMHBIISA-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-glucopyranoside 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：

  phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-glucopyranoside 、 溴甲苯 在 对甲苯磺酸 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 以88 %的产率得到phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-glucopyranoside
  参考文献：
  名称：

  2-脱氧-2-(2,4-二硝基苯磺酰基)-氨基-葡萄糖基/半乳糖基硒糖苷的 β-糖基化：部分 N-乙酰化 β-(1 → 6)-低聚葡萄糖氨基苷的组装

  摘要：

  使用 PhSeCl/AgOTf 作为激活系统，建立了 2-脱氧-2-(2,4-二硝基苯磺酰基)氨基 (2dDNsNH)-吡喃葡萄糖基/吡喃半乳糖基硒糖苷的 β-糖基化的有效方案。该反应的特点是与多种空间位阻或亲核性较差的醇受体进行高度 β-选择性糖基化。硫代糖苷和硒代糖苷基醇被证明是可行的亲核试剂，为一锅法构建低聚糖开辟了新的机会。该方法的强大之处在于，基于具有 DN、邻苯二甲酰基和 2、 2,2-三氯乙氧基羰基作为氨基的保护基。这些聚糖是开发针对微生物感染的糖复合物疫苗的潜在抗原。

  DOI：

  10.1021/acs.joc.3c00725

文献信息

• Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals
  作者：Stanislas Czernecki、Ebtissam Ayadi

  DOI：10.1139/v95-046

  日期：1995.3.1

  6-0-tert-butyldimethylsilyl derivatives as well as with 1,s-anhydro-4,6-0-benzylidene-2-deoxy-d-lyxo- hex-1-enitol and its 3-0-acetyl and 3-0-benzyl derivatives, which were transformed into phenyl2-azido-2- deoxy-a-d-selenogalactopyranoside derivatives in good yield. In the second step, hydrolysis of these selenogly- cosi&s afforded diversely protected glycopyranoses in high yield. Peracetylated derivatives were hydrolyzed

  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
• 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%。
• Crossman Jr., Arthur; Brimacombe, John S.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2769 - 2774
  作者：Crossman Jr., Arthur、Brimacombe, John S.、Ferguson, Michael A. J.

  DOI：——

  日期：——
• 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