benzyl 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-glucopyranoside | 89067-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 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-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 89067-93-6
• 化学式: C₆₃H₅₈N₂O₁₃
• 分子量: 1051.16
• InChiKey: NUCRRXBZEQBRAH-ODVRWTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  78
• 可旋转键数：
  21
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  13

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside	80035-36-5	C35H33NO7	579.65
  b-D-吡喃葡萄糖基氯化,2-脱氧-2-(1,3-二氢-1,3-二羰基-2H-异吲哚-2-基)-3,6-二-O-(苯基甲基)-,4-乙酸酯	4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride	89067-91-4	C30H28ClNO7	550.008

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	benzyl 2-O-benzyl-4,6-O-(R)-benzylidene-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-glucopyranoside	1400810-12-9	C83H78N2O18	1391.53

反应信息

• 作为反应物：
  描述：

  benzyl 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-glucopyranoside 、 methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Thermodynamic Analysis of Interactions between N-Linked Sugar Chains and F-Box Protein Fbs1

  摘要：

  Fbs1 is a recently discovered F-box protein that was proposed to recognize high-mannose-type asparagine-linked glycoprotein sugar chains. To reveal the specificity of Fbs1, Man alpha 1 -> 6Man beta 1 -> 4GlcNAc(2), Man alpha 1 -> 3Mar beta -> 4GlcNAc(2), and Man alpha 1 -> 3(Man alpha 1 -> 6)Man beta 1 -> 4GlcNAc(2) were synthesized and their affinities for Fbs1 were evaluated in comparison with previously synthesized Man(9)GlcNAc(2) and Man(8)GlcNAc(2). These analyses revealed that Man(3)GlcNAc(2) had the strongest affinity and the chitobiose and alpha 1 -> 6 linked Man residue are necessary for Fbs1 to recognize a sugar.

  DOI：

  10.1021/jm0489511
• 作为产物：
  描述：

  phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 lithium hydroxide 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 benzyl 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-glucopyranoside
  参考文献：
  名称：

  Thermodynamic Analysis of Interactions between N-Linked Sugar Chains and F-Box Protein Fbs1

  摘要：

  Fbs1 is a recently discovered F-box protein that was proposed to recognize high-mannose-type asparagine-linked glycoprotein sugar chains. To reveal the specificity of Fbs1, Man alpha 1 -> 6Man beta 1 -> 4GlcNAc(2), Man alpha 1 -> 3Mar beta -> 4GlcNAc(2), and Man alpha 1 -> 3(Man alpha 1 -> 6)Man beta 1 -> 4GlcNAc(2) were synthesized and their affinities for Fbs1 were evaluated in comparison with previously synthesized Man(9)GlcNAc(2) and Man(8)GlcNAc(2). These analyses revealed that Man(3)GlcNAc(2) had the strongest affinity and the chitobiose and alpha 1 -> 6 linked Man residue are necessary for Fbs1 to recognize a sugar.

  DOI：

  10.1021/jm0489511

文献信息

• Chemoenzymatic Approach for the Preparation of Asymmetric Bi-, Tri-, and Tetra-Antennary <i>N</i>-Glycans from a Common Precursor
  作者：Ivan A. Gagarinov、Tiehai Li、Javier Sastre Toraño、Tomislav Caval、Apoorva D. Srivastava、John A. W. Kruijtzer、Albert J. R. Heck、Geert-Jan Boons

  DOI：10.1021/jacs.6b12080

  日期：2017.1.18

  could be obtained by removal of a terminal β-GlcNAc moiety by treatment with β-N-acetylglucosaminidase and selective extension of the other arms. The power of the methodology is demonstrated by the preparation of an asymmetric tetra-antennary N-glycan found in human breast carcinoma tissue, which represents the most complex N-glycan ever synthesized. Multistage mass spectrometry of the two isomeric triantennary

  糖科学的进展因缺乏明确的复杂寡糖标准而受到阻碍，而这些标准是制造下一代微阵列、开发分析方案以确定分离聚糖的精确结构以及阐明聚糖生物合成途径所需的。我们在这里描述了一种化学酶方法，该方法首次使得从单一前体制备任何双触角、三触角和四触角不对称 N-聚糖成为可能。它基于四触角聚糖的化学合成，该四触角聚糖具有 N-乙酰葡糖胺 (GlcNAc)、N-乙酰基乳糖胺 (LacNAc) 和非天然 Galα(1,4)-GlcNAc 和 Manβ(1,4)-GlcNAc 附属物。哺乳动物糖基转移酶仅识别末端 LacNAc 部分作为底物，因此该结构可以独特地延伸。接下来，β-GlcNAc 终端天线可以通过半乳糖基化转化为 LacNAc，然后可以通过酶促修饰成复杂的结构。非天然的 α-Gal 和 β-Man 终止触角可以依次被适当的糖苷酶脱去，以释放末端 β-GlcNAc 部分，该部分可以转化为 LacNAc，然后通过一组糖基转移酶进行加工。通过用
• Synthesis of an octasaccharide fragment of high-mannose-type glycans of glycoproteins
  作者：Tomoo Nukada、Tohru Kitajima、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0008-6215(00)90557-3

  日期：1992.4

  l)-(1----6)-O-(beta-D-mannopyranosyl)-(1----4)-O-( 2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- glucopyranose, an octasaccharide fragment of high-mannose type glycan of glycoproteins, was synthesized. Crucial glycosylation of trisaccharide intermediate, benzyl O-(2,4-di-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-(2-acetamido-3,6-di -O- benzyl-2-deoxy-beta-D-glucopyrano

  O-（α-D-甘露吡喃糖基）-（1 ---- 2）-O-（α-D-甘露吡喃糖基）-（1 ---- 3）-O-[（α-D-甘露吡喃糖基）-（ 1 ---- 2）-O-（α-D-甘露吡喃糖基）-（1 ---- 6）]-O-（α-D-甘露酰吡喃糖基）-（1 ---- 6）-O-（ β-D-甘露吡喃糖基）-（1 ---- 4）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃吡喃糖基）-（1 ---- 4）-2-乙酰氨基-2-脱氧-合成了吡喃葡萄糖，糖蛋白的高甘露糖型聚糖的八糖片段。三糖中间体的关键糖基化，苄基O-（2,4-二-O-苄基-β-D-甘露吡喃糖基）-（1 ---- 4）-O-（2-乙酰氨基-3,6-二-O -苄基-2-脱氧-β-D-吡喃葡萄糖基）-（1 ---- 4）-2-乙酰氨基-3,6-二-O-苯甲酰基-2-脱氧-β-D-吡喃葡糖苷成功仅与二-O-乙酰基十四烷基-O-苄基-D-甘露糖醛酰
• Convergent synthesis of oligomannose-type glycans via step-economical construction of branch structures
  作者：Kanae Sano、Nozomi Ishii、Satoshi Takahashi、Yoichi Takeda、Ichiro Matsuo

  DOI：10.1016/j.carres.2023.108764

  日期：2023.3

  Oligomannose-type glycans on glycoproteins are important signaling molecules in the glycoprotein quality control system in the endoplasmic reticulum. Recently, free oligomannose-type glycans generated by the hydrolysis of glycoproteins or dolichol pyrophosphate-linked oligosaccharides were recognized as important signals for immunogenicity. Hence, there is a high demand for pure oligomannose-type glycans for biochemical

  糖蛋白上的寡甘露糖型聚糖是内质网糖蛋白质量控制系统中的重要信号分子。最近，糖蛋白水解产生的游离寡甘露糖型聚糖或多萜醇焦磷酸连接的寡糖被认为是免疫原性的重要信号。因此，生化实验对纯低聚甘露糖型聚糖的需求量很大；然而，聚糖的化学合成以获得高浓度产品是费力的。在这项研究中，我们展示了一种简单有效的低聚甘露糖型聚糖合成策略。证明了半乳糖基壳二糖衍生物中 2,3,4,6-未保护的半乳糖残基的 C-3 和 C-6 位置的连续区域选择性 α-甘露糖基化。随后，成功地进行了半乳糖部分C-2和C-4位两个羟基的构型反转。该合成路线减少了保护-脱保护反应的次数，适用于构建不同分支模式的低聚甘露糖型聚糖，如 M9、M5A 和 M5B。
• Solving the Convergence Problem in the Synthesis of Triantennary N-Glycan Relevant to Prostate-Specific Membrane Antigen (PSMA)
  作者：Maciej A. Walczak、Samuel J. Danishefsky

  DOI：10.1021/ja307628w

  日期：2012.10.3

  The first total synthesis of triantennary, fully sialylated N-glycan of complex type is described. Two strategies for installation of sialylated antennae are explored, and both approaches converge on a global glycosylation step that delivers the desired tetradecasaccharide in good yields.
• Chemical Synthesis of Highly Congested gp120 V1V2 <i>N</i>-Glycopeptide Antigens for Potential HIV-1-Directed Vaccines
  作者：Baptiste Aussedat、Yusuf Vohra、Peter K. Park、Alberto Fernández-Tejada、S. Munir Alam、S. Moses Dennison、Frederick H. Jaeger、Kara Anasti、Shelley Stewart、Julie H. Blinn、Hua-Xin Liao、Joseph G. Sodroski、Barton F. Haynes、Samuel J. Danishefsky

  DOI：10.1021/ja405990z

  日期：2013.9.4

  Critical to the search for an effective HIV-1 vaccine is the development of immunogens capable of inducing broadly neutralizing antibodies (BnAbs). A key first step in this process is to design immunogens that can be recognized by known BnAbs. The monoclonal antibody PG9 is a BnAb that neutralizes diverse strains of HIV-1 by targeting a conserved carbohydrate protein epitope in the variable 1 and 2 (V1V2) region of the viral envelope. Important for recognition are two closely spaced N-glycans at Asn(160) and Asn(156). Glycopeptides containing this synthetically challenging bis-N-glycosylated motif were prepared by convergent assembly, and were shown to be antigenic for PG9. Synthetic glycopeptides such as these may be useful for the development of HIV-1 vaccines based on the envelope V1V2 BnAb epitope.