ethyl thioglycoside | 187879-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl thioglycoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-(benzenesulfonamido)-6-ethylsulfanyl-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 187879-61-4
• 化学式: C₃₀H₃₅NO₇S₂
• 分子量: 585.742
• InChiKey: FNTILXRRRJWOLL-WYQCABFXSA-N

物化性质

• 沸点：
  707.5±70.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl thioglycoside 在 氨 、 sodium 作用下， 以 甲醇 为溶剂， 生成 乙基3,4,6-三-O-乙酰基-2-乙酰氨基-2-脱氧-beta-D-硫代吡喃葡萄糖苷
  参考文献：
  名称：

  From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide

  摘要：

  DOI：

  10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b
• 作为产物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 在 iodonium(di-γ-collidine) perchlorate 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl thioglycoside
  参考文献：
  名称：

  A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide DomainN-linked to a Natural Peptide Motif

  摘要：

  AbstractN‐Linked glycopeptides were synthesized by condensation of a highmannose anomeric amine bearing a pentasaccharide with aspartic‐acid‐containing tri‐ and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the „core”︁ region of all asparagine‐linked glycoproteins, was assembled by means of glycal‐derived thioethyl donors and glycal acceptors. The central mannose residue was established by inversion of the C2 hydroxyl of a glucosyl precursor in the pentasaccharide. The protecting‐group scheme employed allows the extension of the pentasaccharide through the terminal mannose units. While a fully convergent coupling of the high‐mannose carbohydrate to the peptide domain has thus been accomplished for the first time with a fully synthetic sugar, the stereochemical integrity of the anomeric center of the carbohydrate domain was not maintained and a mixture of glycopeptides was obtained.

  DOI：

  10.1002/chem.19970031011

文献信息

• Nagorny, Pavel; Fasching, Bernhard; Li, Xuechen, Journal of the American Chemical Society, 2009, vol. 131, p. 5792 - 5799
  作者：Nagorny, Pavel、Fasching, Bernhard、Li, Xuechen、Chen, Gong、Aussedat, Baptiste、Danishefsky, Samuel J.

  DOI：——

  日期：——
• Synthesis of the fucosylated biantennary N-glycan of erythropoietin
  作者：Bin Wu、Zihao Hua、J. David Warren、Krishnakumar Ranganathan、Qian Wan、Gong Chen、Zhongping Tan、Jiehao Chen、Atsushi Endo、Samuel J. Danishefsky

  DOI：10.1016/j.tetlet.2006.05.086

  日期：2006.7

  A synthesis of the protected biantennary N-glycan of the naturally occurring glycoprotein. erythropoietin. is described. (c) 2006 Elsevier Ltd. All rights reserved.
• A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
  作者：Zhi-Guang Wang、J. David Warren、Vadim Y. Dudkin、Xufang Zhang、Ulrich Iserloh、Michael Visser、Matthias Eckhardt、Peter H. Seeberger、Samuel J. Danishefsky

  DOI：10.1016/j.tet.2006.02.080

  日期：2006.5

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.