CHIRAL 18-SULPHO-DERIVATIVES OF DEHYDROABIETANE AND A METHOD FOR PRODUCTION THEREOF Russian patent published in 2020 - IPC C07C309/04 

FIELD: chemistry.

SUBSTANCE: invention relates to sulfo-derivatives of dehydroabietane. Described are chiral 18-sulpho-derivatives of dehydroabietane of structural formula (I)

where R is a dehydroabietane structure radical

R¹=-OH; -Cl; -NH₂; -NHEt; -NHEtOH; -NHBn; -NHPh;

where the asterisk denotes a bond, to which a sulpho-group (-SO₂-) is attached. Described is synthesis of sulphonic acid (RCH₂SO₂OH) and sulphochloride (RCH₂SO₂Cl), where R-radical specified above, providing oxidation of dehydroabietanethiol in water-organic solvent with chlorine dioxide (ClO₂), specifically by mixing a thiol solution in an organic solvent with an aqueous or organic chlorine dioxide solution in molar ratio of thiol : ClO₂ equal to 1.0:0.5÷5.0, respectively, for 0.5–4.0 hours, wherein to obtain sulphonic acid water pyridine or dimethylformamide is used as solvent, dichloromethane, water solution of chlorine dioxide and catalyst VO(acac)₂ are used as a solvent for obtaining sulphochloride.

EFFECT: expansion of the arsenal of diterpene sulpho-derivatives of the given structure.

2 cl, 6 ex