FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one, involving: 1) reaction of a compound of formula (II) with a compound of formula (III) in the presence of zinc to obtain a compound of formula (IV); 2) treating the compound of formula (IV) with aqua acid to obtain a compound of formula (V); and 3) cyclisation of the compound of formula (V) in acidic or basic conditions: 
(I) 
(II) 
(III) 
(IV) 
(V), where P' is hydrogen or a protecting group selected from trialkylsilyl and alkoxyalkyl, which is easily removable in acidic conditions, and R is methyl, ethyl or propyl, as well as an intermediate (5R)-2-hexyl-5-hydroxy-3-iminohexadecanoate derivative (V), used in this method and production method thereof. (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one is used in synthesis of oxetanes such as tetrahydrolipstatin.
EFFECT: high output.
13 cl, 4 ex
| Title | Year | Author | Number |
|---|---|---|---|
| METHOD OF PRODUCING (3S,4S)-4-((R)-2-(BENZYLOXY)TRIDECYL)-3-HEXYL-2-OXETANONE AND NOVEL INTERMEDIATE COMPOUND USED IN SAID METHOD | 2009 |
|
RU2471790C1 |
| METHOD OF PRODUCING VORICONAZOLE | 2008 |
|
RU2434009C1 |
| METHOD OF OBTAINING HYDROCHLORIDE OF 1-(3,4-DICHLORO-2-FLUOROPHENYLAMINO)-7-METHOXYQUINAZOLIN-6-YLOXY)PIPERIDIN-1-YL)PROP-2-EN-1-ONE AND INTERMEDIATE COMPOUNDS, APPLIED IN IT | 2012 |
|
RU2563630C1 |
| MACROCYCLIZATION REACTIONS AND INTERMEDIATE COMPOUNDS AND OTHER FRAGMENTS SUITABLE FOR PREPARING ANALOGUES OF HALICHONDRIN B | 2014 |
|
RU2710545C2 |
| C-GLYCOSIDE DERIVATIVES CONTAINING A CONDENSED PHENYL RING, OR THEIR PHARMACEUTICALLY ACCEPTABLE SALTS, A METHOD OF PRODUCING SUCH AND A PHARMACEUTICAL COMPOSITION CONTAINING SUCH | 2017 |
|
RU2739024C2 |
| DPP-IV INHIBITOR CONTAINING BETA AMINO GROUP, METHOD FOR MAKING THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING IT FOR PREVENTION AND TREATMENT OF DIABETES OR OBESITY | 2008 |
|
RU2419615C1 |
| NOVEL TRICYCLIC DERIVATIVE AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, METHOD FOR PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING SAID DERIVATIVE | 2009 |
|
RU2470934C1 |
| METHOD OF PRODUCING MONTELUKAST ACID IN IONIC LIQUID MEDIUM | 2008 |
|
RU2436774C1 |
| METHOD FOR PRODUCING DEPHENYLMETHANE DERIVATIVE | 2017 |
|
RU2797392C2 |
| DERIVATIVES OF QUINOLINE- OR NAPHTHYRIDINE CARBOXYLIC ACID AND METHODS OF THEIR SYNTHESIS | 1995 |
|
RU2120940C1 |
