Thioacetate deprotection

Details Thioacetate deprotection Thioacetate deprotection

2007-02-06

2007-02-06

O'Sullivan, Peter (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

C568S065000, C568S066000, C568S067000, C568S069000, C560S231000

Reexamination Certificate

active

11279153

ABSTRACT:
A method of thioacetate deprotection by providing a compound of the formula R1—S—CO—R2, and reacting the compound with a quaternary ammonium cyanide salt in the presence of a protic solvent in an inert atmosphere to convert the compound to a product of the formula R1—SH. R1is an organic group in which the bonding to sulfur is through a saturated carbon, and R2is an aliphatic group.

REFERENCES:
Gregory et al., “Nucleophilic Displacement Reactions at the Thiol Ester Bond. V. Reactions of 2,2,2-Trifluoroethyl Thiolacetate”J. Am. Chem. Soc., 89(9), 2121-2127 (1967).
Herzig et al., “Studies in Sugar Chemistry. 2. A Simple Method for O-Deacylation of Polyacylated Sugars”J. Org. Chem., 51(5), 727-730 (1986).
Hibbert et al., “Acylation. Part XXIV. The Cyanide Catalysed Hydrolysis of Esters”J. Chem. Soc. B: Phys. Org., 5, 565-568 (1968).
Holmes et al., “Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide”Tetrahedron, 61, 12339-12342 (2005).
Holmes et al., “Thioacetate Deprotection Using Catalytic Tetrabutylammonium Cyanide” MRS Fall 2005 Meeting, Poster Session (Nov. 27, 2005-Dec. 2, 2005).

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