Phenoxythiocarbonyl chloride

To a mixture of cholesterol (0.77 g, 2 mmol) in dichloromethane (10 ml) were added pyridine (0.6 ml, 8 mmol) and phenoxythiocarbonyl chloride (0.4 ml, 2.2 mmol). After 2 h, methanol (1 ml) was added, and the mixture was washed with 1 M HC1 aq. solution twice, then dried over Na2S04. After filtration and removal of the solvent, the residue was recrystallized from acetone to give phenyl thiocarbonate in 95% yield. 

Some reactions follow paths different from the single bond per electrophile sequence. Dibutylstannylene acetals derived from all-tra/is-diols react with phenoxythiocarbonyl chloride at room temperature in 1,4-dioxane to give noncyclic phenylthionocarbonates, but when ds-diols are present, cyclic thionocarbonates spanning the oxygen atoms of the cw-diol are obtained both for pyranosides70 and for furanosides.71... 

In scheme 4, the synthetic route of CNDAC is outlined. Since CNDAC is expected to be base-labile, we started with the N4-acetyl derivative 33, which can be deprotected by acidic hydrolysis. Compound 33 was treated with NaCN in the presence of NaHCOs in aqueous ether57.58 to afford an epimeric mixture of 2 -cyanohydrin 34. Compound 34, without purification, was further treated with phenoxythiocarbonyl chloride in the presence... 

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