phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside | 141193-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside
• 英文别名: phenyl 2,3,4-tri-O-acetyl-6-deoxy-1-thio-β-D-galactopyranoside；Phenyl-2,3,4-tri-O-acetyl-6-desoxy-1-thio-β-D-galactopyranosid；phenyl 2,3,4-tri-O-acetyl-l-thio-β-L-fucopyranoside；phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-2-methyl-6-phenylsulfanyloxan-3-yl] acetate
• CAS: 141193-62-6
• 化学式: C₁₈H₂₂O₇S
• 分子量: 382.434
• InChiKey: YPJGKQRQWRZEKO-YNBLHMCPSA-N

物化性质

• 沸点：
  457.3±45.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside 在 三氟化硼乙醚 、 水 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,4-tri-O-acetyl-6-deoxy-D-galactopyranose
  参考文献：
  名称：

  糖与碳水化合物相互作用的研究：6d-脱氧路易斯x五糖基糖鞘脂的全合成

  摘要：

  本文描述了6d-脱氧Lewis x戊糖基糖鞘脂的全合成，这是研究Lewis x –Lewis x相互作用的有用工具。将6-脱氧半乳糖供体与葡糖胺的二醇缩合以选择性地提供β1→4连接的二糖，将其进一步岩藻糖基化为受保护的脱氧Lewis x三糖。用6d-脱氧Lewis x三糖对乳糖苷二醇进行糖基化，可以以极好的收率选择性和立体选择性地产生五糖。化学修饰后，该五糖与3- O反应-苯甲酰化的叠氮鞘氨醇形成糖鞘脂，在叠氮化物还原后与硬脂酸缩合并脱保护后，得到目标化合物。

  DOI：

  10.1016/j.tet.2010.07.025
• 作为产物：
  描述：

  苯硫酚 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside
  参考文献：
  名称：

  氯甲基糖苷作为制备糖基氧基甲基前药的通用合成子

  摘要：

  在药物分子上引入单糖以提高其溶解度、代谢稳定性和口服生物利用度。开发了一种新的氯甲基糖苷合成子，能够合成多种单糖前药。

  DOI：

  10.1002/chem.202103910

文献信息

• β-Acarbose. VIII.The Synthesis of Some N-Linked Carba-Oligosaccharides
  作者：Matthew G. Tilbrook、Robert V. Stick、Spencer J. Williams

  DOI：10.1071/ch99031

  日期：——

  Two carbohydrate triflates have been used to alkylate a 1-epivalienamine derivative to give small amounts of the desired secondary amines, in addition to amounts of the products of elimination. Deprotection of the secondary amines afforded a carba-disaccharide and a carba-tetrasaccharide which have been shown to be good inhibitors of β-glucosidases.

  用两种碳水化合物三酸酯将 1-环戊二烯胺衍生物烷基化 衍生物进行烷基化，除得到少量所需的仲胺外 消除产物的数量。仲胺的脱保护 仲胺的脱保护作用可得到一种卡巴二糖和一种卡巴四糖。 这两种物质已被证明是 β-葡萄糖苷酶的良好抑制剂。
• The synthesis of deoxy-α-Gal epitope derivatives for the evaluation of an anti-α-Gal antibody binding
  作者：Adam J. Janczuk、Wei Zhang、Peter R. Andreana、Joshua Warrick、Peng G. Wang

  DOI：10.1016/s0008-6215(02)00159-3

  日期：2002.8

  alpha-Gal epitopes (also termed as alpha-Gal) are carbohydrate structures bearing the alpha-D-Gal-(1 --> 3)-beta-D-Gal terminus 1 and are known to be the antigen responsible for antibody-mediated hyperacute rejection in xenotransplantation. Terminal 2-, 3-, 4-, and 6-deoxy-Gal derivatives of alpha-Gal were synthesized. Inhibition ELISA using mouse laminin was established to determine the binding affinity of the synthesized alpha-Gal derivatives. 4-Deoxy-alpha-Gal derivative 7 showed a significant reduction in antibody recognition. The IC50 value was 15-fold poorer than the standard alpha-Gal epitopes alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 --> 4)-beta-D-Glc-NHAc (39) and alpha-D-Gal-(1 --> 3)-beta-D-Gal-(1 -- 4)-beta-D-Glc-OBn (40). A similar observation was seen with 2-deoxy-alpha-Gal derivative 5, whose IC50 value was nearly tenfold higher than the standards. Interestingly, substitution at the terminal 3-position resulted in only a fourfold decrease in antibody recognition, suggesting a possible point of future derivation. Finally, 6-deoxy-alpha-Gal derivative 8 exhibited similar antibody recognition to both alpha-Gal epitope 39 and alpha-Gal epitope 40. This strongly suggests that derivatization at the 6-position can be accomplished without loss of antibody recognition. These findings can be utilized for the future design of other alpha-Gal derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Paulsen, Hans; Rutz, Volker; Brockhausen, Inka, Liebigs Annalen der Chemie, 1992, # 7, p. 747 - 758
  作者：Paulsen, Hans、Rutz, Volker、Brockhausen, Inka

  DOI：——

  日期：——
• Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides
  作者：Jinhua Wang、Jie Li、Hsiao-Nung Chen、Huiwen Chang、Christabel Tomla Tanifum、Hsiu-Hsiang Liu、Przemyslaw G. Czyryca、Cheng-Wei Tom Chang

  DOI：10.1021/jm050368c

  日期：2005.10.1

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.