Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1984-04-04
1985-02-26
Love, Ethel G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549451, 549452, C07D31772
Patent
active
045019096
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
This invention relates to novel aminopolyol derivatives, and more specifically to compounds represented by the following general formula ##STR2## wherein each of R and R' represents a hydrogen atom or an alkyl or aryl group, or R and R', taken together, form an alkylene group, R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or an acyl group, and R.sup.3 represents a lower alkyl group,
The aminopolyol derivatives of general formula (I) are useful as intermediate compounds which can be converted to aminosugars such as daunosamine (which is the sugar moiety of daunomycin useful as an anti-cancer agent), 3-epi.daunosamie, acosamine or ristosamine (see Examples A to E given hereinbelow and Topic in Antibiotic Chemistry, Ellis Horwood, Ltd., Chichester, Vol. 2, pages 99-239, PART C, "Daunomycin and Related Antibiotics" by Federico Arcamone).
BACKGROUND TECHNOLOGY
Prior known methods for synthesizing the aforesaid aminosugars include, for example, (1) those which use sugars as starting materials [see, for example, Topics in Antibiotic Chemistry, Ellis Horwood, Ltd., Chichester, Vol. 2, pages 137-155 and Chem. Comm., 973 (1976)]; (2) those which comprise using petrochemical products as starting materials, subjecting them to stereoselective transformation to obtain the desired products as racemic mixtures [Angew. Chem, 90, 728 (1978) and Bull. Chem. Soc. Jpn., 52, 2731 (1979)]; and (3) those which use optically active naturally occurring materials other than sugars as starting materials [see, for example, Tetrahedron Letters, No. 40, pp. 3883-3886 (1979); ibid., 21, 2999 (1980); ibid., 22, 4017, 5073 (1981); and J. Chem. Soc. Chem. Comm., 442 (1980)]. The methods (1) are advantageous for obtaining optically active compounds because they start from sugars which already have a chiral center. But with these methods, the desired products cannot be obtained unless they go through long steps and therefore, these methods are economically disadvantageous. The key point of the methods (2) is the stereoselective transformation. But no decisive method is available for performing the stereoselective reaction, and another problem is that the final compounds should be optically resolved. At present, the methods (3) seem to be most advantageous for practical purposes. (+)Tartaric acid and D-threonine have been used as starting materials in the methods (3). But when tartaric acid is used as a starting material, the same defect as mentioned with regard to the methods (1) exists. Furthermore, D-threonine itself is not easy to synthesize because its synthesis requires a multiplicity of steps.
DISCLOSURE OF THE INVENTION
The present inventors fully considered the foregoing technical background, and discovered that the compounds of formula (I) which can be derived, for example, from (-)lactate esters or (+)lactate esters are important intermediates which can be easily converted to daunosamine, acosamine, ristosamine, or enantiomers thereof. This discovery has led to the present invention.
The term "lower", used in the present specification and the appended claims, means that a compound or group qualified by this term has not more than 4, preferably not more than 2, carbon atoms.
The "alkyl group" which is represented by R and R' in formula (I) is a linear or branched saturated aliphatic hydrocarbon group, and includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isoamyl and heptyl. Lower alkyl groups are preferred. Examples of the "aryl group" are phenyl, tolyl and naphthyl, phenyl being preferred. The "alkylene group" which can be formed by R and R' may be linear or branched, and preferably has 5 to 12 carbon atoms. Specific examples include hexylene, heptylene, octylene and dodecylene.
On the other hand, the "lower alkyl group" represented by R.sup.1 and R.sup.2 may also be either linear or branched, and includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl and pentyl. R.sup.1 is preferably methyl.
The "acyl group" w
REFERENCES:
patent: 4424370 (1984-01-01), Kleeman et al.
Hiyama Tamejiro
Kobayashi Kazuhiro
Love Ethel G.
Sagami Chemical Research Center
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