Stannylene acetals brominolysis

Another synthesis, described in detail in Scheme 12, was devised specifically for the introduction of deuterium at both ends of l-deoxy-D-t/ireo-pentulose.21,22 Stannylene methodology was used twice, first for glycol splitting with phenyliodonium diacetate, under strictly neutral conditions (necessary to preserve the benzylidene acetal), and secondly to convert the sequence -CHOH-CD3 to CO-CD3 by brominolysis. The final, labeled pentulose was l-deo y-D-threo-(1-2H3, 5-2H)pentulose. 

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