Glycosylation reaction via a mild and efficient one-pot reaction using doped natural phosphate with iodine as catalyst.

Glycosylation reaction via a mild and efficient one-pot reaction using doped natural phosphate with iodine as catalyst.

Nucleosides, nucleotides & nucleic acids (2007-12-07)

H B Lazrek, D Ouzebla, L Baddi, J J Vasseur

ABSTRACT

Several alpha/beta-D-ribonucleosides were synthesized in good yields under mild conditions by N-glycosylations of acetyl 2,3,5-tri-O-benzoyl-beta-D-ribofuranose with silylated nucleobases in acetonitrile using NP doped with iodine as catalyst.

MATERIALS

Product Number

Brand

Product Description

524514

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]yttrium

547980

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]samarium(III), 98%

324620

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide, 97%

702722

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1 M in THF

577928

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in toluene

379212

Sigma-Aldrich

Hexamethyldisilazane, ReagentPlus^®, 99.9%

224367

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in hexanes

324671

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide, 95%

277304

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 0.5 M in toluene

235083

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide, 95%

368059

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 0.6 M in toluene

86944

Sigma-Aldrich

Hexamethyldisilazane, produced by Wacker Chemie AG, Burghausen, Germany, ≥97.0% (GC)

80631

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 40% in THF

577014

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in tert-butyl methyl ether

52619

Supelco

Hexamethyldisilazane, for GC derivatization, LiChropur^™, ≥99.0% (GC)

245585

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 1.0 M in THF

440191

Sigma-Aldrich

Hexamethyldisilazane, reagent grade, ≥99%

225770

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in THF

766917

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.5 M in THF

775061

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1.0 M in 2-methyltetrahydrofuran

766941

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1.0 M in methyl tert-butyl ether

775053

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 0.5 M in 2-methyltetrahydrofuran