benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 61134-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: 2-O-acetyl-1,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；Benzyl 3-O,4-O,6-O-tribenzyl-alpha-D-mannopyranoside acetate；[(2S,3S,4S,5R,6R)-2,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 61134-29-0
• 化学式: C₃₆H₃₈O₇
• 分子量: 582.694
• InChiKey: VFPYLVFMSKNGCQ-DKQOGILZSA-N

物化性质

• 沸点：
  677.2±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 2,4,6-三甲基吡啶 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 sodium 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 benzyl 3,4,6-tri-O-benzyl-2-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  形成肺泡糖蛋白一部分的六糖的合成。

  摘要：

  DOI：

  10.1016/0008-6215(83)88200-7
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 在 mercury dibromide 作用下， 反应 9.0h， 以92 g的产率得到benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of linear d-mannotetraose and d-mannohexaose, partial structures of the cell-surface d-mannan of Candida albicans and Candida utilis

  摘要：

  DOI：

  10.1016/s0008-6215(00)82588-4

文献信息

• Solid-Phase Oligosaccharide Synthesis:  Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents
  作者：Rodrigo B. Andrade、Obadiah J. Plante、Luis G. Melean、Peter H. Seeberger

  DOI：10.1021/ol991071+

  日期：1999.12.1

  [formula: see text] A beta-(1-->4)-linked trisaccharide was prepared in 53% yield on a polymer support using glycosyl phosphates and released by cross-metathesis of a novel linker to reveal the anomeric n-pentenyl glycoside. Heptasaccharide 33 was prepared in 9% yield in 14 steps.

  [公式：参见文本]使用糖基磷酸酯在聚合物载体上以53％的收率制备β-（1-> 4）连接的三糖，并通过新型连接子的复分解而释放，从而揭示异头正戊烯糖苷。通过14个步骤以9％的产率制备七糖33。
• The Glc2Man2-fragment of the N-glycan precursor – a novel ligand for the glycan-binding protein malectin?
  作者：Lisa N. Müller、Claudia Muhle-Goll、Moritz B. Biskup

  DOI：10.1039/c004502k

  日期：——

  The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose.

  合成了天然N-糖苷前体的一个亚结构——Glcα(1→3)Glcα(1→3)Manα(1→2)Man四糖（Glc2Man2-片段）。通过1H15N HSQC实验和等温滴定量热法研究了该片段与定位于内质网的糖结合蛋白malectin的相互作用。Glc2Man2-片段与malectin结合引起的蛋白质主链中核的化学位移扰动暗示了其结合模式类似于已知的配体nigerose。
• Multivalent glyconanoparticles with enhanced affinity to the anti-viral lectin Cyanovirin-N
  作者：Xin Wang、Elena Matei、Lingquan Deng、Olof Ramström、Angela M. Gronenborn、Mingdi Yan

  DOI：10.1039/c1cc12981c

  日期：——

  Low-mannose (LM) structures were coupled to gold nanoparticles (Au NPs) to amplify the affinity of LMs with Cyanovirin-N (CV-N) lectins and to study the structures of CV-N variants CVNQ50C and CVNMutDB.

  将低甘露糖（LM）结构与金纳米粒子（Au NPs）耦合，以放大 LM 与 Cyanovirin-N (CV-N) 凝集素的亲和力，并研究 CV-N 变体 CVNQ50C 和 CVNMutDB 的结构。
• Sonication-Assisted Oligomannoside Synthesis
  作者：Christabel T. Tanifum、Cheng-Wei T. Chang

  DOI：10.1021/jo8019835

  日期：2009.1.16

  We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication-mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activating glycosyl donors that are known to have low reactivity which enable the synthesis of oligomannosides of particular biological interest with the same efficiency.
• Itoh, Yoshio; Tejima, Setsuzo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 3, p. 957 - 966
  作者：Itoh, Yoshio、Tejima, Setsuzo

  DOI：——

  日期：——