Reduction oxathiolane

Table 13 Reductions of Oxathiolanes and Oxathianes with Calcium in Liquid Ammonia " ...

Mechanistic studies have led to a proposed pathway for formation of the oxathiolanone 220 in low yield by electrochemical reduction in the presence of H2S (Equation 79) <1996T1259>. No reasonable mechanism has yet been suggested for the formation of oxathiolane 221 (Equation 80) <1995KGS1694, 1997RJ0395>. 

As with the oxathiolane, direct cleavage of the cis diols of 122 with NalO. followed by NaBH4 reduction and reaction with TsOH in acetone, gave the isopropylidene derivative 123 (Scheme 24). Protection of the remaining hydroxyl as its benzoate, followed by removal of the isopropylidene group, gave the protected dioxolane diol 124. 

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