ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide | 329365-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
• 英文别名: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyldisulfide；(2S,3R,4S,5R,6R)-2-(ethyldisulfanyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 329365-86-8
• 化学式: C₃₆H₄₀O₅S₂
• 分子量: 616.843
• InChiKey: ZVFFFDREYXUPHH-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 在 三丁基膦 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 0.08h， 以95%的产率得到2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration

  摘要：

  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,.

  DOI：

  10.1021/jo051374j
• 作为产物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 在 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
  参考文献：
  名称：

  糖基苯硫基磺酸盐（glyco-PTS）：糖蛋白合成的新型试剂。

  摘要：

  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。

  DOI：

  10.1039/b306990g

文献信息

• Glycosyldisulfides: a new class of solution and solid phase glycosyl donors
  作者：Benjamin G. Davis、Sarah J. Ward、Phillip M. Rendle

  DOI：10.1039/b008734n

  日期：——

  Mixed glycosyl disulfides are not only glycomimetics but also glycosyl donors that may be readily constructed in either armed ether-protected or disarmed ester-protected and in soluble or solid-supported forms from corresponding glycosyl methanethiosulfonates and used in the glycosylation of a variety of representative acceptors.

  混合糖基二硫化物不仅是糖模拟物，而且是糖基供体，可以很容易地以武装醚保护或解除武装酯保护的形式构建，并以相应的糖基甲硫代磺酸盐以可溶或固体支持的形式构建，并用于各种代表性受体的糖基化.
• A Coordinated Synthesis and Conjugation Strategy for the Preparation of Homogeneous Glycoconjugate Vaccine Candidates
  作者：Elizabeth J. Grayson、Gonçalo J. L. Bernardes、Justin M. Chalker、Omar Boutureira、Julia R. Koeppe、Benjamin G. Davis

  DOI：10.1002/anie.201006327

  日期：2011.4.26

  A sweet solution: A strategy for the synthesis of well‐defined carbohydrate‐based vaccines is presented. The approach couples complex oligosaccharide synthesis to site‐specific conjugation methodology to provide pure glycoprotein vaccine candidates (see scheme).

  一个甜蜜的解决方案：提出了一种合成明确定义的基于碳水化合物的疫苗的策略。该方法将复杂的寡糖合成与位点特异性结合方法相结合，以提供纯糖蛋白候选疫苗（见方案）。
• [EN] REAGENTS AND METHODS FOR THE FORMATION OF DISULFIDE BONDS AND THE GLYCOSYLATION OF PROTEINS<br/>[FR] REACTIFS ET PROCEDES POUR FORMER DES LIAISONS DISULFURE ET POUR GLYCOSYLER DES PROTEINES
  申请人：ISIS INNOVATION

  公开号：WO2005000862A3

  公开（公告）日：2005-08-18
• 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,.
• 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。