methyl 3,4-di-O-benzyl-6-O-triphenylmethyl-2-acetamido-2-deoxy-a-D-glucopyranoside | 69892-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 3,4-di-O-benzyl-6-O-triphenylmethyl-2-acetamido-2-deoxy-a-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(trityloxymethyl)oxan-3-yl]acetamide
• CAS: 69892-50-8
• 化学式: C₄₂H₄₃NO₆
• 分子量: 657.807
• InChiKey: PGWKVJIPQIKKOC-LRHJBHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-6-O-triphenylmethyl-2-acetamido-2-deoxy-a-D-glucopyranoside 在 4-二甲氨基吡啶 、 硫酸 、 氢溴酸 、 mercury(II) sulfate 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 N-[(1S,2R,3S,6S)-2,3-dibenzyloxy-6-hydroxy-4-oxocyclohexyl]acetamide
  参考文献：
  名称：

  N-乙酰氨基葡糖衍生的5a-氨基糖类似物作为糖苷酶抑制剂的设计与合成

  摘要：

  描述了从N-乙酰氨基葡糖开始高效合成L型和D型新的六元碳环糖的方法。关键的合成步骤包括区域选择性保护和脱保护，费耶碳环化，Peterson烯烃化，硼氢化和立体选择性环氧化，然后是区域选择性环氧开环反应。这些六元石斑显示出适度的糖苷酶抑制活性，并且发现其中一种化合物对β-半乳糖苷酶抑制活性具有选择性。

  DOI：

  10.1016/j.tet.2018.02.063
• 作为产物：
  描述：

  甲基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 在 吡啶 、 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 123.0h， 生成 methyl 3,4-di-O-benzyl-6-O-triphenylmethyl-2-acetamido-2-deoxy-a-D-glucopyranoside
  参考文献：
  名称：

  Roy, Abhijit; Ray, Asim K.; Mukherjee, Atryee, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1165 - 1167

  摘要：

  DOI：

文献信息

• Synthetic development of sugar amino acid oligomers towards novel podophyllotoxin analogues
  作者：Megan Bouchard、Thomas Tremblay、Marie-Pier Paré-Lacroix、Mathieu Gagné-Boulet、Sébastien Fortin、Denis Giguère

  DOI：10.1016/j.bmc.2021.116501

  日期：2021.12

  the synthesis of sugar amino acid oligomers based on the glucosamine scaffold. We found that the solid-phase approach was unsuccessful for the preparation of sugar amino acid oligomers and the limitation of the liquid-phase approach revolved around the low solubility of larger oligomers. Nevertheless, this strategy allowed the coupling of alkynylated carbohydrate amino acids with podophyllotoxin-bearing

  在这项工作中，我们开发了一种基于氨基葡萄糖支架合成糖氨基酸低聚物的方法。我们发现固相方法无法成功制备糖氨基酸低聚物，液相方法的局限性在于较大低聚物的低溶解度。然而，该策略允许将炔基化碳水化合物氨基酸与带有叠氮官能团的鬼臼毒素偶联，产生新的鬼臼毒素类似物。由于它们的低溶解度，抗增殖研究表明这些新合成的类似物没有抗癌活性。
• A versatile carbohydrate based gelator for oil water separation, nanoparticle synthesis and dye removal
  作者：Chintam Narayana、Ravi Kant Upadhyay、Raman Chaturvedi、Ram Sagar

  DOI：10.1039/c6nj03520e

  日期：——

  conditions. Hydrogel prepared using the gelator was further explored as reaction medium for the growth of gold nanoparticles. In the case of nanoparticle synthesis, the gelator served not only as a capping agent but also as a reducing agent. By taking advantage of the dual functionality of the gelator (capping and reducing agent), nanoparticles of both gold and silver were prepared in fluid medium

  据报道，一种适用于多种应用的多功能绿色胶凝剂。在极短的胶凝时间（<5 s）内实现了有机溶剂的胶凝。研究了冷却和超声处理对胶凝时间的影响。除有机溶剂外，该胶凝剂还可以与柴油和汽油等燃料形成凝胶。因此，它已经用于通过油的选择性胶凝从油/水混合物中分离油。还发现该胶凝剂能够通过合理控制反应条件来形成水凝胶。进一步探索了使用胶凝剂制备的水凝胶作为金纳米颗粒生长的反应介质。在纳米颗粒合成的情况下，胶凝剂不仅用作封端剂，而且还用作还原剂。通过利用胶凝剂（封端剂和还原剂）的双重功能，还可以在流体介质中制备金和银的纳米颗粒。使用甲苯和胶凝剂制备的有机凝胶用于去除水性合成染料若丹明B.
• DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis
  作者：Lars Petersen、Knud J. Jensen

  DOI：10.1039/b105872j

  日期：——

  The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH2Cl2 or nitromethane in the presence of LiClO4. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl3, TMSOTf, or BF3·Et2O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO4 gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.

  报告了在高效的路易斯酸促进糖基化反应中使用 DISAL（二硝基水杨酸甲酯）糖基供体的情况。在 CH2Cl2 或硝基甲烷中，在 LiClO4 的存在下，使用苄基和苯甲酰基保护的 DISAL 给体成功地在 O-6 或 O-4 处糖基化了 N-乙酰基-D-氨基葡萄糖单糖受体。由此分离出的二糖收率在 35% 到 93% 之间。其他路易斯酸（如 FeCl3、TMSOTf 或 BF3-Et2O）也被证明能有效地对仲醇环己醇进行糖基化。不过，在合成二糖时，LiClO4 的温和活化可获得更高的产量。这种方法扩展到了通过骨架酰胺连接物（BAL）将 2-氨基锚定在聚苯乙烯支架上的 D-氨基葡萄糖衍生物的高效固相糖基化。
• Stereoselective Preparation of Deuterium-Labeled Sugars:  (6<i>R</i>)-(6-²H₁)-<i>N</i>-Acetylglucosamine Derivatives
  作者：Margaret L. Falcone-Hindley、Jeffery T. Davis

  DOI：10.1021/jo980781a

  日期：1998.8.1

  The preparation of methyl (6R)-(6-H-2(1))-2-deoxy-2-N-acetamido-alpha-D-glucose (8 alpha-d) and methyl (6R)-(6-H-2(1))-2-deoxy-2-N-acetamido-beta-D-glucose (8 beta-d) is described. The key step in the synthesis was the stereoselective reduction of a C6-aldehydo-GlcNAc derivative with (R)-(+)-Alpine-Borane-d. Reduction of either methyl 6-aldehydo-3,4-di-O-benzyl-alpha-GlcNAc (6 alpha) or methyl 6-aldehydo-3,4-di-O-benzyl-beta-GlcNAc (6 beta) using (R)-(+)-Alpine-Borane-d in CH2Cl2 was significantly more stereoselective (>15:1 stereoselectivity for both anomers) than was reduction with NaBD4 in MeOH. The absolute stereochemistry at C6 of the deuterated GlcNAc derivatives was determined from H-1 NMR analysis of the conformationally locked sugars, methyl (6R)-(6-H-2(1))-4,6-O-benzylidene-2-deoxy-2 N-acetamido-alpha-D-glucose (9 alpha-d) and methyl (6R)-(6-H-2(1))-4,6-O-benzylidene-2-deoxy-2- beta-D-glucose (9 beta-d). Comparison of (3)J(H5,H6) values and H-1-H-1 NOEs for the nondeuterated and deuterated benzylidene derivatives showed that reduction with (R)-(+)-Alpine-Borane-d gave the (6R)-(6-H-2(1)) epimer as the major product for both the GlcNAc alpha and beta methyl glycosides. This stereoselective reduction enabled the H-1 NMR signals for the prochiral H6 and H6' protons in a series of GlcNAc derivatives to be assigned.
• ROY, ABHIJIT;RAY, ASIM K.;MUKHERJEE, ATRYEE;ROY, NIRMOLENDU, INDIAN J. CHEM. B., 26,(1987) N2, C. 1165-1167
  作者：ROY, ABHIJIT、RAY, ASIM K.、MUKHERJEE, ATRYEE、ROY, NIRMOLENDU

  DOI：——

  日期：——