Methanol → HCID 136330638, compound

Participants

Reaction Steps

Compound (59) is repeatedly dried by evaporating off anhydrous pyridine. 400 mg (0.87 mmol) of compound (59) which has been dried in this way are dissolved in 5 ml of anhydrous pyridine. After adding 4,4′-dimethoxytrityl chloride (328 mg, 0.95 mmol) at room temperature, the reaction mixture is stirred overnight. MeOH (3 ml) and 5% aq. NaHCO3 (30 ml) are then added. The aqueous phase is extracted 3 times with CH2Cl2. The organic phase is dried (Na2SO4) and evaporated, and the residue is subjected to flash chromatography (column: 10×5 cm, solvent CH2Cl2/acetone, 9:1). Isolating the material from the main zone affords the colorless, amorphous title compound (61). (600 mg, 91%). 1H-NMR ([D6] DMSO: δ=1.13 (m, 4 CH3), 2.24 (m, H—C(2′)), 2.77 (m, CH), 3.12 (m, H—C(5′)), 3.75 (s, 2 CH3O), 3.93 (m, H—C(4′)), 4.35 (m, H—C(3′)), 5.30 (d, 3′-OH), 6.39 (dd, H—C(1′)), 6.86-7.39 (m, aromatic H +H—C(6)), 11.54, 11.82 (2s, 2 NH). Anal. calculated for C36H37JN4O7 (764.6): C 56.55, H 4.88, N 7.33: found C 56.42, H 4.82, N 7.30.

Provenance & Evidence