p-nitrophenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide | 870472-12-1

• 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: p-nitrophenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
• 英文别名: p-nitrophenyl(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)disulfide；(2S,3R,4S,5R,6R)-2-[(4-nitrophenyl)disulfanyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 870472-12-1
• 化学式: C₄₀H₃₉NO₇S₂
• 分子量: 709.884
• InChiKey: QSFGGXBDWMUPPD-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 在 三丁基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到p-nitrophenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  从二硫键连接到硫醚连接的糖蛋白。

  摘要：

  DOI：

  10.1002/anie.200704381
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-glucopyranosyl methanethiosulfonate 、 4-硝基苯硫醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到p-nitrophenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
  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

文献信息

• From Disulfide- to Thioether-Linked Glycoproteins
  作者：Gonçalo J. L. Bernardes、Elizabeth J. Grayson、Sam Thompson、Justin M. Chalker、James C. Errey、Farid El Oualid、Timothy D. W. Claridge、Benjamin G. Davis

  DOI：10.1002/anie.200704381

  日期：2008.3.7
• 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,.