1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 68567-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranose；1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranose；[(2R,3S,4S,5R,6R)-2-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 68567-54-4
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: SHXWXUTXYNDCRM-YOGXEWEVSA-N

物化性质

• 沸点：
  626.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.33h， 生成 methyl 4-[(2R,3S,4S,5R,6R)-3-[[(3aS,5R,6R,7S,7aS)-2-methyl-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybenzoate
  参考文献：
  名称：

  使用甘露糖基碘化物供体1高效合成Man 2，Man 3和Man 5寡糖。

  摘要：

  已经开发了使用正交保护的糖基碘碘供体制备Man 3和Man 5寡糖的高效方案。C-2- O的糖基化在-40°C的三氟甲磺酸银存在下，β-乙酰基甘露糖基碘化物供体开始生成所需的α-连接的甘露糖苷和原乙酸酯的混合物，该混合物由对C-2乙酸酯的攻击引起。但是，温热至室温后，原乙酸酯定量地重排为所需的寡糖。使用3，6-二羟基受体并使其经受双重糖苷化作用，很快就以几乎定量的产量提供了高甘露糖。糖基碘化物供体比先前报道的氯化物供体具有优势，因为反应更快，产率更高并且在高阶构建体中不会减少。这些研究继续消除了糖基碘化物反应性太强以至于不能用于合成的观念。

  DOI：

  10.1021/jo051360d
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 吡啶 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 生成 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015

文献信息

• Preparation of Thiosugars and Their Use
  申请人：Davis Benjamin Guy

  公开号：US20090176970A1

  公开（公告）日：2009-07-09

  A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

  一种制备由糖硫代糖（Saccharide-S-H）表示的硫代糖的方法，其中糖代表至少4个糖单元，包括将具有以下结构的相应化合物（P）糖硫代糖（P）进行桦还原：（P）糖硫代糖（P），其中（P）代表一个或多个O-或S-保护基。
• Synthetic trisaccharides reveal discrimination of<i>endo</i>-glycosidic linkages by<i>exo</i>-acting α-1,2-mannosidases in the endoplasmic reticulum
  作者：Kyohei Nitta、Taiki Kuribara、Kiichiro Totani

  DOI：10.1039/d1ob00428j

  日期：——

  the Man9GlcNAc2 glycan is that all terminal glycosidic linkages of the three branches are of the α-1,2 type, while the adjacent inner glycosidic linkages are different. In this study, we examined whether the α-1,2-mannosidases showed branch specificity by discriminating between different inner glycosides. Four trisaccharides with different glycosidic linkages [Manα1-2Manα1-2Man (natural A-branch), Manα1-2Manα1-3Man

  内质网 (ER) 糖蛋白表面的三触角 Man 9 GlcNAc 2聚糖在区域选择性裂解每个分支的末端 α-1,2-甘露糖残基后充当糖蛋白分泌或降解信号。四种 α-1,2-甘露糖苷酶——ER 甘露糖苷酶 I、ER 降解增强 α-甘露糖苷酶样蛋白 1 (EDEM1)、EDEM2 和 EDEM3——参与这些信号聚糖的产生。尽管信号聚糖的选择性产生对于决定糖蛋白的命运很重要，但α-1,2-甘露糖苷酶的分支辨别能力尚不清楚。 Man 9 GlcNAc 2聚糖的结构特征是三个分支的所有末端糖苷键都是α-1,2型，而相邻的内部糖苷键不同。在本研究中，我们通过区分不同的内糖苷来检查 α-1,2-甘露糖苷酶是否表现出分支特异性。具有不同糖苷键的四种三糖[Manα1-2Manα1-2Man（天然A分支）、Manα1-2Manα1-3Man（天然B分支）、Manα1-2Manα1-6Man（天然C分支）和Man
• 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.
• C2-Acyloxyglycosylation with Glycal Donors
  作者：Lei Shi、Yong-Jae Kim、David Y. Gin

  DOI：10.1021/ja015991a

  日期：2001.7.1
• Du, Yuguo; Kong, Fanzuo, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 341 - 352
  作者：Du, Yuguo、Kong, Fanzuo

  DOI：——

  日期：——