p-Methoxyphenyl (MP) Glycosides with a Stable and Easily Removable Protecting Group

Protecting groups at the anomeric position in the chemical synthesis of sugar chains require stability to reaction conditions such as glycosidation and selective deprotection capability for inducing glycosyl donors. The p-methoxyphenyl (MP) group is suitable for the requirements and is widely used for sugar chain synthesis.^1,2) The deprotection of MP glycosides by ammonium cerium(IV) nitrate gives the 1-OH form, which can be induced to the following glycosyl fluorides and glycosyl imidates. In addition, MP glycosides can be converted into glycosyl halides and thioglycosides in one step.³⁾ TCI offers a wide range of MP glycosides including not only monosaccharides like 4-methoxyphenyl β-D-glucopyranoside but also oligosaccharides like Gb₃-β-MP for sugar chain synthesis.

Related Products

C1806

Ammonium Cerium(IV) Nitrate

M1631

4-Methoxyphenyl β-D-Glucopyranoside

M1767

Gb₃-β-MP

Product Category Page

• MP Glycosides [Glyco Building Blocks]

References

• 1) A highly stereoselective and practical synthesis of cyclomannohexaose, Cyclo{→4)-[α-D-Manp-(1→4)-]₅-α-D-Manp-(1→}, a manno isomer of cyclomaltohexaose
  • M. Mori, Y. Ito, T. Ogawa, Carbohydr. Res. 1989, 192, 131.
• 2) Stereoselective total synthesis of the blood group I-active biantennary neolacto-glycodecaosyl ceramide
  • Y. Matsuzaki, Y. Ito, T. Ogawa, Tetrahedron Lett. 1992, 33, 4025.
• 3) Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides
  • Z. Zhang, G. Magnusson, Carbohydr. Res. 1996, 295, 41.

Page Top