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57099-04-4

1,2-O-ISOPROPYLIDENE-3-BENZYLOXY-D-ALLOFURANOSE synthesis

9synthesis methods
-

Yield:57099-04-4 95%

Reaction Conditions:

with acetic acid in water at 20; for 72 h;

Steps:

1,2-Di-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose (12)

To acetic acid (2 L) and water (0.5 L) was added 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (500 g,1.43 mol) and the mixture was left to stand at room temperature for 72 h. The solution was then poured into an ice-coldsolution of sodium hydroxide (1.5 kg) in water (7.5 L) with vigorous stirring and addition of ice to keep the temperature below 20 °C. The mixture was then extracted with ethyl acetate (2 x 2.5 L) and the combined organics were washed with brine, dried over magnesium sulfate, combined with a second batch carried out on the same scale and concentrated under reduced pressure to give 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (921 g, 95%) as a yellow oil.

References:

Chapron, Christopher;Glen, Rebecca;La Colla, Massimiliano;Mayes, Benjamin A.;McCarville, Joseph F.;Moore, Stephen;Moussa, Adel;Sarkar, Ruhul;Seifer, Maria;Serra, Ilaria;Stewart, Alistair [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 12,p. 2699 - 2702]