1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose

• 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: 1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R)-3,4-dibenzoyloxy-6-hydroxy-5-phenylmethoxyoxan-2-yl]methyl benzoate
• 化学式: C₃₄H₃₀O₉
• 分子量: 582.607
• InChiKey: MWMUWFPDXDLHKZ-OHSUJLOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose 在 甲醇 、 18-冠醚-6 、 乙酰溴 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.5h， 生成 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate
  参考文献：
  名称：

  Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation

  摘要：

  It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in

  DOI：

  10.1021/ol1023079
• 作为产物：
  描述：

  (S)-((2S,3R,4S,5R,6R)-4,5-bis(benzoyloxy)-6-((benzoyloxy)methyl)-3-(benzyloxy)tetrahydro-2H-pyran-2-yl)(ethyl)(methyl)sulfonium trifluoromethanesulfonate 反应 16.0h， 生成 1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  非对映异构纯糖基锍盐的直接合成

  摘要：

  据报道，稳定的糖基锍盐可以通过乙基硫糖苷的直接异头 S-甲基化产生。从机制上讲，该途径代表了硫代糖苷类糖苷化活化的第一步；然而，它可以进一步合成和分离准稳定的锍离子，代表了研究这些关键中间体的新方法。

  DOI：

  10.1021/ol2009818

文献信息

• Comprehensive synthesis of ER related high-mannose-type sugar chains by convergent strategy
  作者：Ichiro Matsuo、Kiichiro Totani、Atsushi Tatami、Yukishige Ito

  DOI：10.1016/j.tet.2006.06.045

  日期：2006.8

  Systematic synthesis of high-mannose-type sugar chains of asparagine-linked glycoproteins is described. To construct the target sugar chains, we employed the convergent route, using three oligosaccharide components, the common hexasaccharide, branched tri-, tetra- and pentasaccharides, and mono-, di-, and triglucosyl fragments. Construction of the β-mannoside linkage was performed using p-methoxybenzyl-assisted

  描述了天冬酰胺连接的糖蛋白的高甘露糖型糖链的系统合成。为了构建目标糖链，我们采用了收敛途径，使用了三种低聚糖成分：普通六糖，支链三糖，四糖和五糖以及单糖，二糖和三糖基片段。使用p进行β-甘露糖苷键的构建-甲氧基苄基辅助的分子内糖苷配基递送。将六糖片段与支链甘露寡糖供体（例如M5，M4B，M4C和M3）偶联，分别得到十一碳糖（M9），十糖（M8B和M8C）和九糖（M7）。结合它们的单，二和三葡萄糖基片段分别得到十四碳糖（G3M9），十三碳糖（G2M9），十二碳糖（G1M9），十一碳糖（G1M8B和G1M8C）和十碳糖（G1M7）。
• Regioselectivity in the reductive ring-opening reaction of 1,2-O-benzylidene sugars
  作者：Katsuhiko Suzuki、Hisato Nonaka、Masanori Yamaura

  DOI：10.1016/s0040-4039(03)00068-6

  日期：2003.2

  Regioselectivity in the ring-opening reaction of 1,2-O-benzylidene sugars was studied. In the reductive ring-opening reaction of 1,2-O-benzylidene derivatives, only a CO1 bond was cleaved in the case of manno-type, but both the CO1 and CO2 bonds were cleaved in the case of gluco-type.

  研究了1,2- O-亚苄基糖在开环反应中的区域选择性。在1，2- O-亚苄基衍生物的还原性开环反应中，在甘露型的情况下，仅C 1 O 1键被断裂，而在C 2 O 1和C 3 O 2键均被断裂。葡萄糖型的情况。
• Revisiting the Armed−Disarmed Concept:  The Importance of Anomeric Configuration in the Activation of <i>S</i>-Benzoxazolyl Glycosides
  作者：David Crich、Ming Li

  DOI：10.1021/ol701466u

  日期：2007.10.1

  The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.
• First chemical synthesis of triglucosylated tetradecasaccharide (Glc3Man9GlcNAc2), a common precursor of asparagine-linked oligosaccharides
  作者：Ichiro Matsuo、Toshinori Kashiwagi、Kiichiro Totani、Yukishige Ito

  DOI：10.1016/j.tetlet.2005.04.056

  日期：2005.6

  Triglucosylated high-mannose-type tetradeca saccharide (Glc(3)Man(9)GlcNAc(2)), the oligosaccharide part of the donor substrate of oligosaccharyl transferase (OST) complex, and diglucosylated tridecasaccharide (Glc(2)Man(9)GlcNAc(2)) were synthesized. These oligosaccharides were assembled in a convergent and stereoselective manner. Undecasaccharide 5 was employed as the common intermediate, and coupling with trisaccharide (4) and disaccharide (3) donor afforded fully protected tetradeca-(17) and tridecasaccharide (16), respectively. These oligosaccharides were deprotected to give Glc(3)Man(9)GlcNAc(2) and Glc(2)Man(9)GlcNAc(2), respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• Direct Synthesis of Diastereomerically Pure Glycosyl Sulfonium Salts
  作者：Laurel K. Mydock、Medha N. Kamat、Alexei V. Demchenko

  DOI：10.1021/ol2009818

  日期：2011.6.3

  glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can further allow for the synthesis and isolation of quasi-stable sulfonium ions, representing a new approach for studying these key intermediates.

  据报道，稳定的糖基锍盐可以通过乙基硫糖苷的直接异头 S-甲基化产生。从机制上讲，该途径代表了硫代糖苷类糖苷化活化的第一步；然而，它可以进一步合成和分离准稳定的锍离子，代表了研究这些关键中间体的新方法。