benzyl (2-(tert-butoxycarbonylamido)ethyl)-N,N-diisopropylphosphoramidite | 1023637-24-2

• 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: benzyl (2-(tert-butoxycarbonylamido)ethyl)-N,N-diisopropylphosphoramidite
• 英文别名: benzyloxy-[2-(tert-butyloxycarbonylamino)ethoxy]-(N,N-diisopropylamino)phosphine；2-(tert-butyloxycarbonylamino)ethyl benzyl N,N-diisopropylphosphoramidite；2-(N-Boc-amino)ethyl benzyl N,N-diisopropylphosphoramidite；tert-butyl N-[2-[[di(propan-2-yl)amino]-phenylmethoxyphosphanyl]oxyethyl]carbamate
• CAS: 1023637-24-2
• 化学式: C₂₀H₃₅N₂O₄P
• 分子量: 398.483
• InChiKey: GIULMLUFCUXARS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (2-(tert-butoxycarbonylamido)ethyl)-N,N-diisopropylphosphoramidite 在 四氮唑 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.17h， 生成 benzyl 2-O-(dibenzylphosphono)-6-O-((benzyl)-(2-dodecanamidoethyl)phospono)-3,4-dihydroxyl-β-D-galactopyranoside
  参考文献：
  名称：

  D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成

  摘要：

  New-to-Nature D-半乳糖基溶血磷脂经过合理设计和合成，可作为磷脂酰肌醇磷酸激酶的人工底物和非 ATP 竞争性抑制剂，磷脂酰肌醇磷酸激酶是经过验证的致命人类疾病（包括癌症、肌萎缩侧索硬化和 SARS- COVID-2 感染。D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成（X. Huang、J. Hu 等人）

  DOI：

  10.1002/chem.202202083
• 作为产物：
  描述：

  苯甲醇 在 二异丙基铵盐四氮唑 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 benzyl (2-(tert-butoxycarbonylamido)ethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成

  摘要：

  New-to-Nature D-半乳糖基溶血磷脂经过合理设计和合成，可作为磷脂酰肌醇磷酸激酶的人工底物和非 ATP 竞争性抑制剂，磷脂酰肌醇磷酸激酶是经过验证的致命人类疾病（包括癌症、肌萎缩侧索硬化和 SARS- COVID-2 感染。D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成（X. Huang、J. Hu 等人）

  DOI：

  10.1002/chem.202202083

文献信息

• Synthesis of phosphorylated 3,4-branched trisaccharides corresponding to LPS inner core structures of Neisseria meningitidis and Haemophilus influenzae
  作者：Johan D.M. Olsson、Stefan Oscarson

  DOI：10.1016/j.carres.2010.03.006

  日期：2010.7

  spacer-equipped protected derivative of the common 3,4-branched diheptoside trisaccharide structure of the lipopolysaccharide core of Neisseria meningitidis and Haemophilus influenzae has been synthesized. The protecting group pattern installed allows regioselective introduction of phosphoethanolamine residues in the 3- and 6-position of the second heptose unit in accordance with native structures. From this intermediate

  2-（N-苄氧基羰基）氨基乙基7-O-乙酰基-6-O-烯丙基-2-O-苯甲酰基-4-O-苄基-3-O-氯乙酰基-1-甘油-α-d-manno-庚基吡喃糖基-（1-> 3）-[2,3,4,6-四-O-苯甲酰基-β-d-吡喃葡萄糖基-（1-> 4）] -6,7-二-O-乙酰基-2已经合成了脑膜炎奈瑟氏球菌和流感嗜血杆菌的3，4-支化二庚糖苷三糖结构的具有间隔基的被保护的衍生物-O-苄基-1-甘油-α-d-甘露聚糖-吡喃果糖苷。所安装的保护基图案允许根据天然结构在第二个庚糖单元的3位和6位区域选择性引入磷酸乙醇胺残基。
• Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures
  作者：Karin Mannerstedt、Eva Segerstedt、Johan Olsson、Stefan Oscarson

  DOI：10.1039/b717564g

  日期：——

  A conserved tetrasaccharide structure, L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-aminoethylphosphono-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose, from the LPS inner core of Haemophilus influenzae has been synthesised as its ethylamino glycosides to allow later conjugations. Starting from a previously synthesised suitably protected trisaccharide intermediate, the third heptose and subsequently the spacer were introduced using thioglycoside donor chemistry. The phosphoethanolamine was formed employing a Boc-protected phosphoamidite. Final deprotection and conjugation to biotin gave conjugates that will be used to study the specificity of MAbs raised against native LPS structures.

  一种保守的四糖结构，L-glycero-α-D-manno-heptopyranosyl-(1→2)-(6-O-氨乙基膦酸-L-glycero-α-D-manno-heptopyranosyl)-(1→3)-[β-D-glucopyranosyl-(1→4)]-L-glycero-α-D-manno-heptopyranose，已从流感嗜血杆菌的LPS内核中合成为其乙基氨基糖苷，以便于后续的连接。从先前合成的适当保护的三糖中间体开始，引入了第三个七碳糖，随后通过硫糖苷供体化学引入了连接体。磷酸乙醇胺是通过使用Boc保护的磷酸酰胺化合物形成的。最后去保护并与生物素连接，得到的结合物将用于研究针对天然LPS结构的单克隆抗体的特异性。
• Zwitterionic Phosphodiester-Substituted Neoglycoconjugates as Ligands for Antibodies and Acute Phase Proteins
  作者：Karell Pérez Labrada、Sebastian Strobl、Barbara Eckmair、Markus Blaukopf、Zuzanna Dutkiewicz、Alba Hykollari、Daniel Malzl、Katharina Paschinger、Shi Yan、Iain B. H. Wilson、Paul Kosma

  DOI：10.1021/acschembio.9b00794

  日期：2020.2.21

  Zwitterionic modifications of glycans, such as phosphorylcholine and phosphoethanolamine, are known from a range of prokaryotic and eukaryotic species and are recognized by mammalian antibodies and pentraxins; however, defined saccharide ligands modified with these zwitterionic moieties for high-throughput studies are lacking. In this study, we prepared and tested example mono- and disaccharides 6-substituted with either phosphorylcholine or phosphoethanolamine as bovine serum albumin neoglycoconjugates or printed in a microarray format for subsequent assessment of their binding to lectins, pentraxins, and antibodies. C-Reactive protein and anti-phosphorylcholine antibodies bound specifically to ligands with phosphorylcholine, but recognition by concanavalin A was abolished or decreased as compared with that to the corresponding nonzwitterionic compounds. Furthermore, in array format, the phosphorylcholine-modified ligands were recognized by IgG and IgM in sera of either non-infected or nematode-infected dogs and pigs. Thereby, these new compounds are defined ligands which allow the assessment of glycan-bound phosphorylcholine as a target of both the innate and adaptive immune systems in mammals.
• Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures
  作者：Johan D.M. Olsson、Stefan Oscarson

  DOI：10.1016/j.tetasy.2009.02.017

  日期：2009.5

  A phosphoethanolamine-substituted tetrasaccharide structure, 2-aminoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 2)-6-O-[2-(tert-butyloxycarbonylaminoethyl)-phophono]-L-glycero-alpha-D-manno-heptopyranosyl-(1 -> 3)-[beta-D-glucopyranosyl-(1 -> 4)]-L-glycero-alpha-D-manno-heptopyranoside,corresponding to the non-reducing part of the conserved part of Neisseria meningitidis lipopolysaccharides has been synthesized. Orthogonal protection of the phosphoethanolamino group in combination with the presence of a free amino-containing anomeric spacer allows conjugation to proteins to construct conjugate vaccine candidates. The tetrasaccharide is built up using a linear strategy, where the introduction Of the terminal alpha-GlcNAc moiety is performed using a 2-azido-thioglucoside as a donor and NIS/AgOTf as a promoter. The synthetic pathway includes tetrasaccharide intermediates appropriately designed to permit other phosphorylation patterns as well as elongation at the reducing end. (C) 2009 Elsevier Ltd. All rights reserved.
• Rational Design and Synthesis of D‐galactosyl Lysophospholipids as Selective Substrates and non‐ATP‐competitive Inhibitors of Phosphatidylinositol Phosphate Kinases
  作者：Mengxia Sun、Chi Zhang、Dexin Sui、Canchai Yang、Dohun Pyeon、Xuefei Huang、Jian Hu

  DOI：10.1002/chem.202202083

  日期：2023.1.9

  and non-ATP-competitive inhibitors of phosphatidylinositol phosphate kinases, which are validated drug targets for deadly human diseases including cancers, amyotrophic lateral sclerosis, and SARS-COVID-2 infection. Rational Design and Synthesis of D-galactosyl Lysophospholipids as Selective Substrates and non-ATP-competitive Inhibitors of Phosphatidylinositol Phosphate Kinases (X. Huang, J. Hu et al

  New-to-Nature D-半乳糖基溶血磷脂经过合理设计和合成，可作为磷脂酰肌醇磷酸激酶的人工底物和非 ATP 竞争性抑制剂，磷脂酰肌醇磷酸激酶是经过验证的致命人类疾病（包括癌症、肌萎缩侧索硬化和 SARS- COVID-2 感染。D-半乳糖基溶血磷脂作为磷脂酰肌醇磷酸激酶的选择性底物和非 ATP 竞争性抑制剂的合理设计和合成（X. Huang、J. Hu 等人）