(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-ol | 185446-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4R,5R,6R)-2-methylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 185446-93-9
• 化学式: C₂₈H₃₂O₅S
• 分子量: 480.625
• InChiKey: OYMLBZSFRILBDH-CRWBFSFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-ol 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-phenol
  参考文献：
  名称：

  Ito, Yukishige; Kanie, Osamu; Ogawa, Tomoya, Angewandte Chemie, 1996, vol. 108, # 21, p. 2691 - 2693

  摘要：

  DOI：
• 作为产物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl chloride 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  通过分子内苷元递送 (IAD) 对 2-O-烯丙基保护的糖基供体进行立体选择性顺式糖基化

  摘要：

  2-O-烯丙基保护的糖基供体可以通过涉及双键异构化、N-碘代琥珀酰亚胺介导的与糖基受体的束缚和随后的分子内糖基化（分子内苷元递送，IAD）的三步序列进行立体选择性糖基化。

  DOI：

  10.1039/b004522p

文献信息

• Stereoselective 1,2-cis Glycosylation of 2-O-Allyl Protected Thioglycosides
  作者：Mahmoud Aloui、David J. Chambers、Ian Cumpstey、Antony J. Fairbanks、Alison J. Redgrave、Christopher M. P. Seward

  DOI：10.1002/1521-3765(20020603)8:11<2608::aid-chem2608>3.0.co;2-4

  日期：2002.6.3

  intramolecular aglycon delivery (IAD), whereby a glycosyl acceptor is temporarily appended to a hydroxyl group of a glycosyl donor is an attractive method that can allow the synthesis of 1,2-cis glycosides in an entirely stereoselective fashion. 2-O-Allyl protected thioglycoside donors are excellent substrates for IAD, and may be glycosylated stereoselectively through a three-step reaction sequence. This sequence

  分子内糖苷配基递送（IAD）技术，其中将糖基受体暂时附加到糖基供体的羟基上，是一种有吸引力的方法，它可以以完全立体选择性的方式合成1,2-顺式糖苷。2-O-烯丙基保护的硫代糖苷供体是IAD的优异底物，可通过三步反应序列进行立体选择性糖基化。该序列由定量产生的烯丙基键异构化组成，以产生乙烯基醚，该乙烯基醚随后可以进行所需的糖基受体的N-碘代琥珀酰亚胺介导的束缚，以及随后的分子内糖基化，从而相应地产生α-葡糖苷或β-甘露糖苷。尽管一锅连接和糖基化的尝试因与过量糖基受体之间的竞争性分子间反应而受阻，这个问题可以通过使用过量的糖基供体简单地克服。烯丙基介导的IAD是其他IAD合成β-甘露糖苷的方法的一种广泛适用的实用替代方法，该方法同样适用于α-葡萄糖键。就施用的简便性和产率而言，这是有利的，此外，不需要糖基供体的环状4，6-保护。
• 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）。
• Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions
  作者：Akihiro Ishiwata、Ayaka Sakurai、Katharina Dürr、Yukishige Ito

  DOI：10.1016/j.bmc.2010.04.013

  日期：2010.6.1

  Rate acceleration of O-glycosylation had been observed in p-xylene under frozen conditions, when thioglycosides were activated by methyl trifluoromethane sulfonate. Curiously, significant perturbation of stereoselectivity was observed. Effects of various factors, such as solvent, concentration, anomeric configuration and protective groups of the donor, were systematically examined to clarify the mechanistic implications of stereoselectivity on glycosylation under frozen system. Our study revealed that the stereoselectivity was affected by concentration both in liquid as well as in frozen conditions, indicating that rate acceleration effect in frozen solvent was caused by highly concentrated environments. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin
  作者：Ichiro Matsuo、Megumi Wada、Shino Manabe、Yoshiki Yamaguchi、Keisuke Otake、Koichi Kato、Yukishige Ito

  DOI：10.1021/ja021288q

  日期：2003.3.1

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.
• Synthesis of complex-type glycans derived from parasitic helminths
  作者：Jun Nakano、Hiromichi Ohta、Yukishige Ito

  DOI：10.1016/j.bmcl.2005.10.100

  日期：2006.2

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.