Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside | 153808-91-4

• 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-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-5-azido-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylselanyloxane
• CAS: 153808-91-4
• 化学式: C₃₃H₃₃N₃O₄Se
• 分子量: 614.603
• InChiKey: XBLAAOVLJTTYST-IZDBAANZSA-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-galactopyranoside 在 吡啶 、 1,3-丙二硫醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 生成 Phenyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
  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：

  苯基硒基-2-叠氮基-3,4,6-三-O-乙酰基-α-D-吡喃半乳糖苷 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 31.0h， 生成 Phenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside
  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

• Further probing of the substrate specificities and inhibition of enzymes involved at an early stage of glycosylphosphatidylinositol (GPI) biosynthesis
  作者：Arthur Crossman、Michael J. Paterson、Michael A.J. Ferguson、Terry K. Smith、John S. Brimacombe

  DOI：10.1016/s0008-6215(02)00187-8

  日期：2002.11

  been prepared and tested in cell-free assays as substrate analogues/inhibitors of alpha-(1 --> 4)-D-mannosyltransferases that are active early on in the glycosylphosphatidylinositol (GPI) biosynthetic pathways of Trypanosoma brucei and HeLa (human) cells. The corresponding N-acetyl derivatives of these compounds were similarly tested as candidate substrate analogues/inhibitors of the N-deacetylases present

  对这些化合物的相应N-乙酰基衍生物进行了类似测试，作为两种系统中存在的N-脱乙酰基酶的候选底物类似物/抑制剂。根据早期研究，1-L-6-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-2-O-甲基-肌醇1-（1,2-二-O制备了（十六烷酰基-sn-甘油3-磷酸酯）（44），并作为锥虫α-（1-4）-D-甘露糖基转移酶的抑制剂进行了测试。提供了各种类似物的生物学评估的简要概述。
• 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%。
• Radical mediated synthesis of containing C-disaccharides via a temporary phosphoramidic connection
  作者：Gilles Rubinstenn、Jacques Esnault、Jean-Maurice Mallet、Pierre Sinaÿ

  DOI：10.1016/s0957-4166(97)00141-9

  日期：1997.4

  The C-disaccharide α-d-GalNAc-C-(1→)-β-d-Glc-OMe} and its interglycosidic β anomer were synthesized by radical coupling of phenyl onto methyl , which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl to produce the two closely related α-OMe C-disaccharides.

  所述Ç -disaccharide α-d-的GalNAc-C-（1→）-β-d-GLC-OME}及其interglycosidicβ端基异构体是由苯基的自由基偶联合成到甲基，其通过磷酰氨系绳临时连接。类似的反应用甲基进行，以产生两个密切相关的α-OME Ç -disaccharides。
• Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides
  作者：Liming Wang、Yongzhen Zhang、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1021/acs.joc.0c00703

  日期：2020.12.18

  A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-α-(1,4)-glucosazide]

  引入了一种新的添加剂，甲基（苯基）甲酰胺（MPF），用于2-叠氮基-2-脱氧葡萄糖结构单元的糖基化。组装了线性α-（1,4）-氨基葡萄糖四糖以证明MPF的实用性。接下来，使用由MPF调节的[2 + 2 + 2]策略组装铜绿假单胞菌胞外多糖Pel的六糖片段。使用的4,6- O- DTBS保护的半乳糖基叠氮化物供体合成了使用过的[半乳糖叠氮化物-α-（1,4）-葡糖叠氮化物]二糖结构单元。
• 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。