(2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-6-methylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol | 104992-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-6-methylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 104992-65-6
• 化学式: C₂₁H₂₄O₅S
• 分子量: 388.485
• InChiKey: JPCMGXOFVXLTOL-RLLAOZKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-6-methylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 1-piperidinecarbodithioate 在 2,6-二叔丁基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以79%的产率得到methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl 1-piperidinecarbodithioates in the synthesis of glycosides

  摘要：

  DOI：

  10.1016/0008-6215(91)84154-7

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）。
• 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.