(2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate | 1242060-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: p-tolyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-galactopyranoside；4-Methylphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-galactopyranose；[(2R,3R,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl acetate
• CAS: 1242060-83-8
• 化学式: C₂₁H₂₇NO₈S
• 分子量: 453.513
• InChiKey: AVNPTGOQJCORAS-ADAARDCZSA-N

物化性质

• 沸点：
  612.8±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 p-tolyl 2-amino-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Additive-Controlled Stereoselective Glycosylations of Oxazolidinone-Protected Glucosamine and Galactosamine Thioglycoside Donors Based on Preactivation Protocol

  摘要：

  根据预激活方案，可通过添加剂控制噁唑烷酮保护的氨基糖硫代糖苷给体对糖基化的立体选择性。通过改变添加剂可获得δ-或δ-选择性。2,4,6-三叔丁基嘧啶（TTBP）是最好的δ-定向添加剂，而噻吩则是最好的δ-定向添加剂。双功能添加剂，如四丁基碘化铵（TBAI），根据添加量的不同，可提供δ-或δ-选择性。添加 TBAI 或噻吩后，一些未添加任何添加剂的糖基化反应的δ-选择性大大提高。

  DOI：

  10.1055/s-0030-1258557
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 四氯化锡 作用下， 反应 8.08h， 生成 (2R,3R,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  A Facile and Efficient Method for the One-Pot Synthesis of Per-O-acetylated Thioglycosides from Unprotected Sugars

  摘要：

  An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.

  DOI：

  10.1080/07328303.2012.673669

文献信息

• Stable Amide Activation of <i>N</i>-Acetylated Glycosamines for the Synthesis of Fused Polycyclic Glycomimetics
  作者：Samaneh Zarei、Mélina Motard、Samy Cecioni

  DOI：10.1021/acs.orglett.3c03803

  日期：2024.1.12

  underexplored target for chemoselective derivatization and generation of glycomimetic scaffolds. Through mild amide activation, we report that N-acetimidoyl heterocycles are stable in neutral or basic conditions yet are excellent leaving groups through acid catalysis. While this specific reactivity could prove broadly useful in amide activation strategies, stably activated N-acetylated sugars can also be diversified

  碳水化合物的N-乙酰化是化学选择性衍生化和糖模拟支架生成的一个尚未充分探索的靶标。通过温和的酰胺活化，我们报告N-乙酰亚氨基杂环在中性或碱性条件下是稳定的，并且通过酸催化是优异的离去基团。虽然这种特定的反应性可能在酰胺活化策略中广泛有用，但也可以使用酰肼库使稳定活化的N-乙酰化糖多样化。我们优化了酸催化的一锅法序列，包括亲核置换、环脱水和分子内糖基化，最终产生与吗啉或哌嗪融合的吡喃糖苷。这种稳定激活后进行酸触发反应序列的策略例证了富含 3D 的融合糖模拟文库的有效组装。
• Synthesis and immunological study of a wall teichoic acid-based vaccine against <i>E. faecium</i> U0317
  作者：Zhifang Zhou、Wenzhang Ding、Chen Li、Zhimeng Wu

  DOI：10.1080/07328303.2017.1390576

  日期：2017.6.13

  A repeat unit of cell wall teichoic acids (WTA) isolated from E. faecium U0317 was chemically synthesized efficiently by a stepwise strategy. It was derivatized with a 5-aminopentanyl linker to facilitate conjugation with carrier proteins KLH and HSA. Immunological studies of the KLH conjugate 1 demonstrated that it could provoke robust immune responses and high titers of IgG antibodies, which could successfully recognize the synthesized WTA repeat unit 3. This result suggested that synthetic glycoconjugate 1 could be a promising vaccine candidate against E. faecium for further studies.
• A highly α-selective glycosylation for the convenient synthesis of repeating α-(1→4)-linked N-acetyl-galactosamine units
  作者：Lin Yang、Xin-Shan Ye

  DOI：10.1016/j.carres.2010.05.031

  日期：2010.8

  The repeating GalpNAc-alpha-(1 -> 4)-GalpNAc unit is part of a series of essential structures that can be found in many important biomolecules such as the glycoproteins and the O-antigenic polysaccharides of clinically important bacterial strains. In this paper, we describe an exclusive alpha-selective glycosylation reaction, using a 4,6-di-O-tert-butyldimethylsilyl-N-acetyloxazolidinone-protected thioglycoside as the glycosyl donor, under pre-activation conditions, with only half amount of the promoter, providing the product GalpNAc-alpha-(1 -> 4)-GalpNAc in high isolated yield. This reaction can be also applied to increasing the length of the repeating structure, which is of significant use in further synthesis of branched or linear oligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.