beta-D-Ribofuranoside, methyl 2,3,5-tris-O-[(2,4-dichlorophenyl)methyl]- → 1-o-Methyl-3,5-bis-o-(2,4-dichlorobenzyl)-beta-d-ribofuranose

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Step 1 (171.60 g, 0.2676 mol) in 1.8 L of methylene chloride that was cooled to 0° C., was added dropwise a solution of stannous chloride (31.522 mL, 0.2676 mol) in 134 mL of methylene chloride while stirring. After maintaining the solution at about 3° C. for approximately 27 hours, another 5.031 mL of stannous chloride (SnCl4) (0.04282 mol) was added and the solution was kept at about 3° C. overnight. After a total reaction time of approximately 43 hours, the reaction was quenched by carefully adding the solution to 1.9 L of a saturated NaHCO3 solution. Tin salts were removed via filtration through Celite after which the organic phase was isolated, dried with MgSO4 and evaporated in vacuo. The yield of raw, dark yellow oil was 173.6 g. The crude oil was used directly in the next step without further purification.

Provenance & Evidence