3,6-di-O-benzyl-4-O-[3',6'-di-O-benzyl-4'-O-(2'',4''-di-O-benzyl-β-D-mannopyranosyl)-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl azido | 172316-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-benzyl-4-O-[3',6'-di-O-benzyl-4'-O-(2'',4''-di-O-benzyl-β-D-mannopyranosyl)-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl azido
• 英文别名: azido-2,4-di-O-benzyl-β-D-mannopyranosyl(1→ 4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside；2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide；2-[(2R,3R,4R,5S,6R)-2-azido-5-[(2S,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-5-[(2S,3S,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3,5-bis(phenylmethoxy)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 172316-09-5
• 化学式: C₇₆H₇₃N₅O₁₇
• 分子量: 1328.44
• InChiKey: HXNVAICSBMYXHQ-LTYMFQLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  98
• 可旋转键数：
  28
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  231
• 氢给体数：
  2
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-4-O-[3',6'-di-O-benzyl-4'-O-(2'',4''-di-O-benzyl-β-D-mannopyranosyl)-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl azido 、 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride 在 二氯二茂锆 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以83%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-[2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  用于固相糖肽合成的双天线配合物类型的非糖基Asn构件的合成

  摘要：

  以适合于Fmoc固相肽合成研究的受保护形式合成带有LacNAc和LacdiNAc作为非还原末端基序的双天线复合型N-聚糖。通过利用GlcNTCA（N-苯基）三氟乙酰亚氨酸酯的高度β-选择性糖基化作用，研究了两种合成九糖的方法。较早的方法涉及三糖供体（Gal-GlcNTCA-Man）和三糖受体（Man-GlcNPhth 2 -N 3）的反应，产生了九糖异构体的混合物。另一方面，三糖受体的甘露糖基化（Man-GlcNPhth 2 -N 3）立体选择性地得到已知的五糖（Man 3 -GlcNPhth 2 -N 3），其与二糖基糖基供体（Gal-GlcNTCA或GalNTCA-GlcNTCA）反应以产生所需的九糖为单个立体异构体。选择性脱酞酰化，然后进行N-乙酰化，提供了GlcNAc 2的功能。在Ph（CH 3）2 P和HOOBt存在下，将所得的非糖基叠氮化物与Fmoc-Asp（OPfp）-OBu

  DOI：

  10.1021/jo200149d
• 作为产物：
  描述：

  azido-2-O-benzyl-3-O-p-methoxy-benzyl-4,6-O-benzylidine-β-Dmannopyranosyl(1→4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1→4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三乙基硅烷 、 二氯苯酚溴酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 以95%的产率得到3,6-di-O-benzyl-4-O-[3',6'-di-O-benzyl-4'-O-(2'',4''-di-O-benzyl-β-D-mannopyranosyl)-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl azido
  参考文献：
  名称：

  用于固相糖肽合成的双天线配合物类型的非糖基Asn构件的合成

  摘要：

  以适合于Fmoc固相肽合成研究的受保护形式合成带有LacNAc和LacdiNAc作为非还原末端基序的双天线复合型N-聚糖。通过利用GlcNTCA（N-苯基）三氟乙酰亚氨酸酯的高度β-选择性糖基化作用，研究了两种合成九糖的方法。较早的方法涉及三糖供体（Gal-GlcNTCA-Man）和三糖受体（Man-GlcNPhth 2 -N 3）的反应，产生了九糖异构体的混合物。另一方面，三糖受体的甘露糖基化（Man-GlcNPhth 2 -N 3）立体选择性地得到已知的五糖（Man 3 -GlcNPhth 2 -N 3），其与二糖基糖基供体（Gal-GlcNTCA或GalNTCA-GlcNTCA）反应以产生所需的九糖为单个立体异构体。选择性脱酞酰化，然后进行N-乙酰化，提供了GlcNAc 2的功能。在Ph（CH 3）2 P和HOOBt存在下，将所得的非糖基叠氮化物与Fmoc-Asp（OPfp）-OBu

  DOI：

  10.1021/jo200149d

文献信息

• 6-Nitro-2-benzothiazolyl α-Mannoside: A Highly Efficient Mannosyl Donor in Constructing β-Man(1→4)GlcN Linkage and Its Application to the Synthesis of the Pentasaccharide Core of<i>N</i>-Glycans
  作者：Hiroki Mandai、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.479

  日期：2006.3

  An efficient and concise synthesis of the β-Man(1→4)GlcN linkage that exists in N-linked glycans has been established. Direct β-mannosylations of the 4-OH group of glucosamine derivatives by using ...

  已经建立了存在于 N-连接聚糖中的 β-Man(1→4)GlcN 键的高效简明合成。葡萄糖胺衍生物的 4-OH 基团的直接 β-甘露糖基化...
• One-Pot Glycosylation Strategy Assisted by Ion Mobility–Mass Spectrometry Analysis toward the Synthesis of <i>N</i>-Linked Oligosaccharides
  作者：Kalyana Kumar Ponnapalli、Yi-Chi Ho、Mei-Chun Tseng、Bhanu Vijaya Sekhar Vasamsetti、Jiun-Jie Shie

  DOI：10.1021/acs.joc.2c00184

  日期：2022.4.15

  for the synthesis of N-glycans are crucial for the rapid generation of pure samples to determine their biological functions. Herein, we describe a double one-pot strategy for the synthesis of N-glycans assisted by an IM–MS analysis approach for rapid screening of optimized glycosylation reaction conditions. This research includes triflate-mediated direct β-mannosylation and tandem glycosylation in a one-pot

  N-聚糖是几种细胞糖蛋白的主要成分。N-聚糖合成的一锅法对于快速生成纯样品以确定其生物学功能至关重要。在此，我们描述了一种通过 IM-MS 分析方法辅助合成N-聚糖的双一锅策略，用于快速筛选优化的糖基化反应条件。这项研究包括三氟甲磺酸酯介导的直接 β-甘露糖基化和串联糖基化，采用一锅法合成具有挑战性的N-连接三糖核心β-5。此外， N-连接三糖核心的一锅顺序糖基化7提供多种高甘露糖型N-聚糖，具有出色的立体选择性和区域选择性。特别是，应用离子淌度-质谱定量分析来确定粗反应混合物的立体选择性和区域选择性结果，以开发高效的一锅法。
• Synthesis of Fully<i>O</i>-Benzylated<i>N</i>-Linked Core Pentasaccharide Glycosyl Azide
  作者：László Kalmár、Károly Ágoston、Zoltán Szurmai、Boglárka Döncző、János Kerékgyártó

  DOI：10.1080/07328303.2011.642433

  日期：2012.3

  The fully O-benzylated pentasaccharide glycosyl azide representing the common core structure of N-glycans was synthesized. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via DMSO/Ac2O oxidation followed by stereoselective reduction with tetrabutylammonium borohydride.
• Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate
  作者：Zhong-Wu Guo、Yuko Nakahara、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0968-0896(97)00126-0

  日期：1997.10

  The intact peptide sequence (18) as well as its glycoform carrying an N-linked core pentasaccharide (I) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligo saccharide-asparagine conjugate (3) as building blocks. It was concluded that the pentasaccharide structure had little influence on further peptide elongation in solid-phase synthesis and the benzylated pentasaccharide moiety was sufficiently stable to the 95% TFA acidic conditions used to release glycopeptide from the supporting resin. The paper also describes an efficient route leading to asparagine-core pentasaccharide conjugate (3) which was prepared in seven steps for an overall yield of 23% from monosaccharide units 5, 6, 7 and 8. (C) 1997 Elsevier Science Ltd.
• A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a key building block for the synthesis of complex N-linked glycopeptides
  作者：Zhong-Wu Guo、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0040-4039(97)01036-8

  日期：1997.7

  The complex-type biantennary heptasaccharide-asparagine conjugate(2) of N-linked glycoproteins was synthesized from monosaccharide units 3, 4, 6, 7 and 8 in 7 steps with an overall yield of 18.4%. (C) 1997 Elsevier Science Ltd.