S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) methanethiosulfonate | 398469-69-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) methanethiosulfonate
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl methanethiosulfonate；Gal(Ac)4β-MTS；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-methylsulfonylsulfanyloxan-2-yl]methyl acetate
• CAS: 398469-69-7
• 化学式: C₁₅H₂₂O₁₁S₂
• 分子量: 442.465
• InChiKey: IQLJSXWXOFAZAS-FQKPHLNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) methanethiosulfonate 在 sodium methylate 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 18.17h， 生成 methyl 4-S-(β-D-galactopyranosyl-1'-thio)-4-thio-α-D-glucopyranoside
  参考文献：
  名称：

  糖苷间键中含有二硫化物和硒硫化物官能团的二糖类似物的合成和构象分析

  摘要：

  含二硫化物（甲基-4-S-（β-D-吡喃半乳糖基-1'-硫代）-4-硫代-α-D-吡喃葡萄糖苷（1））和硒代硫化物（甲基-4-Se-（）的新型二糖的合成描述了 β-D-吡喃半乳糖基-1'-硫代)-4-硒-α-D-吡喃葡萄糖苷 (2)) 在糖苷间键合中的功能。合成策略依赖于 β-糖基硫代磺酸盐与碳水化合物硫醇或硒醇亲核试剂的反应。将得到的受保护的 β-二杂连接的二糖脱保护以得到目标化合物。这些二杂类似物的构象偏好是从 NOESY 实验和变温 NMR 光谱中的谱线加宽效应推断出来的，并根据分子轨道理论进行了合理化。

  DOI：

  10.1139/v05-107
• 作为产物：
  描述：

  D-吡喃葡萄糖 以47%的产率得到S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) methanethiosulfonate
  参考文献：
  名称：

  [EN] REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS
  [FR] REACTIFS ET PROCEDES POUR FORMER DES LIAISONS DISULFURE ET POUR GLYCOSYLER DES PROTEINES

  摘要：

  公开号：

  WO2005000862A3

文献信息

• Glycosyl phenylthiosulfonates (Glyco-PTS): novel reagents for glycoprotein synthesisThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.Electronic supplementary information (ESI) available: experimental procedures, characterization, protein ESI-MS spectra and crystal data. See http://www.rsc.org/suppdata/ob/b3/b306990g/
  作者：David P. Gamblin、Philippe Garnier、Sarah J. Ward、Neil J. Oldham、Antony J. Fairbanks、Benjamin G. Davis

  DOI：10.1039/b306990g

  日期：——

  Controlled site-selective glycosylation can be achieved by combining site-directed cysteine mutagenesis with chemical modification of the introduced thiol; a new class of more efficient chemoselective reagents, glycosyl phenylthiosulfonates, allow rapid glycosylations of representative simple thiols, peptides and proteins.

  通过将定点半胱氨酸诱变与引入的硫醇的化学修饰相结合，可以实现受控的位点选择性糖基化。新型的更有效的化学选择试剂，糖基苯基硫代磺酸盐，可以使代表性的简单硫醇，肽和蛋白质快速糖基化。
• WO2006/55437
  申请人：——

  公开号：——

  公开（公告）日：——
• Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration
  作者：Elizabeth J. Grayson、Sarah J. Ward、Alison L. Hall、Phillip M. Rendle、David P. Gamblin、Andrei S. Batsanov、Benjamin G. Davis

  DOI：10.1021/jo051374j

  日期：2005.11.1

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.