peracetyl 4-methylphenyl 1-thio-β-D-maltopyranoside | 27894-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: peracetyl 4-methylphenyl 1-thio-β-D-maltopyranoside
• 英文别名: p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside；p-tolyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside；4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-Oacetyl-β-D-glucopyranoside；b-D-Glucopyranoside, 4-methylphenyl4-O-(2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl)-1-thio-, triacetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(4-methylphenyl)sulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 27894-92-4
• 化学式: C₃₃H₄₂O₁₇S
• 分子量: 742.752
• InChiKey: XPESVSIBQABDCQ-JUJWBDIVSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  738.4±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  51
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  peracetyl 4-methylphenyl 1-thio-β-D-maltopyranoside 在 甲醇 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以99%的产率得到(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  合成带有带有不同保护基的麦芽糖侧链的三个OSW-1类似物。

  摘要：

  为了简化OSW-1的二糖侧链的合成并探索OSW-1的结构-活性关系，设计并合成了三个带有三个具有不同保护基的麦芽糖侧链的16α - O-麦芽糖OSW-1类似物。

  DOI：

  10.1080/10286020.2013.863185
• 作为产物：
  描述：

  麦芽糖 在 三氟化硼乙醚 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 生成 peracetyl 4-methylphenyl 1-thio-β-D-maltopyranoside
  参考文献：
  名称：

  合成带有带有不同保护基的麦芽糖侧链的三个OSW-1类似物。

  摘要：

  为了简化OSW-1的二糖侧链的合成并探索OSW-1的结构-活性关系，设计并合成了三个带有三个具有不同保护基的麦芽糖侧链的16α - O-麦芽糖OSW-1类似物。

  DOI：

  10.1080/10286020.2013.863185

文献信息

• Large‐scale Synthesis of Per‐<i>O</i>‐acetylated Saccharides and Their Sequential Transformation to Glycosyl Bromides and Thioglycosides
  作者：Li‐Cheng Huang、Pi‐Hui Liang、Ching‐Yang Liu、Chun‐Cheng Lin

  DOI：10.1080/07328300600770469

  日期：2006.6

  This work describes a large‐scale synthesis of per‐O‐acetylated mono‐ and disaccharides using a stoichiometric amount of acetic anhydride in the presence of LiClO4 under solvent‐free conditions. The peracetylated saccharides underwent subsequent anomeric bromination and thioglycosidation in one‐pot to yield synthetically valuable building blocks.

  这项工作描述了在无溶剂条件下，在LiClO4存在下，使用化学计量的乙酸酐大规模合成过O-乙酰化的单糖和二糖。过乙酰化的糖随后在一个锅中进行异头溴化和硫糖苷化反应，以产生具有合成价值的结构单元。
• Mild and Efficient Hydrolysis of Thioglycosides to Glycosyl Hemiacetals Using <i>N</i>-Iodosaccharin
  作者：Anup Misra、Pintu Mandal

  DOI：10.1055/s-2007-977412

  日期：——

  A convenient methodology has been developed for the mild hydrolysis of thioglycosides to the corresponding hemiacetals using N-iodosaccharin without any requirement of co-activator. Most of the functional groups used for the protecting group ­manipulation of carbohydrates remain unaffected under the reaction conditions.

  已开发出一种便捷的方法，利用N-碘代糖精在无需任何共活化剂的条件下对硫苷进行温和水解，生成相应的半缩醛。在反应条件下，大多数用于糖类保护基操作的功能团保持不受影响。
• Boron-Promoted Umpolung Reaction of Sulfonyl Chlorides for the Stereospecific Synthesis of Thioglycosides via Reductive Deoxygenation Coupling Reactions
  作者：Siyu Li、Yujuan Wang、Lei Zhong、Siyu Wang、Zhengli Liu、Yuanwei Dai、Yun He、Zhang Feng

  DOI：10.1021/acs.orglett.2c00353

  日期：2022.4.8

  potential. Herein we disclose an efficient method for the stereospecific synthesis of 1-thioglycosides via a boron-promoted reductive deoxygenation coupling reaction from readily accessible sulfonyl chlorides and glycosyl bromides. Our protocol features mild conditions and excellent functional group tolerance and stereoselectivity. The translational potential of this metal-free approach is demonstrated

  S-糖苷具有广泛的生物活性并作为天然O-糖苷对应物的稳定模拟物，因此具有巨大的治疗潜力。在这里，我们公开了一种通过硼促进的还原脱氧偶联反应从容易获得的磺酰氯和糖基溴化物立体定向合成 1-硫糖苷的有效方法。我们的协议具有温和的条件和出色的官能团耐受性和立体选择性。这种无金属方法的转化潜力通过天然产物和药物分子的后期糖多样化得到证明。
• Lanthanum Trifluoromethane-sulfonate‐Catalyzed Facile Synthesis of Per‐<i>O</i>‐acetylated Sugars and Their One‐Pot Conversion to <i>S</i>‐Aryl and <i>O</i>‐Alkyl/Aryl Glycosides
  作者：Somnath Dasgupta‡、Vishal Kumar Rajput‡、Bimalendu Roy、Balaram Mukhopadhyay

  DOI：10.1080/07328300701298170

  日期：2007.4.30

  Lanthanum trifluoromethanesulfonate- catalyzed solvent-freeper-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.[GRAPHICS]
• Stereoselective Syntheses of 1,2-trans<i>p</i>-MePh and 2-Pyridyl 1-Thioglycosides Catalyzed by Zirconium(IV) Chloride
  作者：Yili Ding

  DOI：10.1080/00397919908085987

  日期：1999.10

  1-Thioglycosides including per-O-acetyl p-MePh and 2-pyridyl 1-thioglycosides were chemically synthesized with high complete stereoselectivity by using ZrCl4 as catalyst.