Method of preparing trans-3,4-disubstituted-.gamma.-lactones

Details Method of preparing trans-3,4-disubstituted-.gamma.-lactones Method of preparing trans-3,4-disubstituted-.gamma.-lactones

1991-05-03

1993-06-01

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30733

Patent

active

052161773

ABSTRACT:
First, levoglucosenone is made to react with methyl lithium in the presence of copper iodide in order to introduce a methyl group into an enone group of levoglucosenone, and to obtain 1,6-anhydro-3,4-dideoxy-4-C-methyl-.beta.-D-erythro-hexopyranose-2-ulose. This methyl compound is oxidized in acetic acid for lactone formation, and (3S,4S)-5-hydroxy-3-methylpentan-4-olide is thus obtained. Further, this lactone is made to react with tosyl chloride in anhydrous pyridine to obtain (3S,4S)-3-methyl-5-tosyloxypentan-4-olide (tosylate). The obtained tosylate is alkylated with n-propyl lithium in the presence of copper iodide to obtain (3S,4R)-3-methyl-4-octanolide. Here, the (3S,4S)-3-methyl-5-tosyloxypentan-4-olide may be treated with potassium carbonate to cleave lactone ring once, thereby obtaining epoxide. After that, the obtained epoxide is alkylated to form lactone ring again to obtain (3S,4R)-3-methyl-4-octanolide.

REFERENCES:
patent: 3926947 (1975-12-01), Lipska
March, J. Advanced Org. Chem., pp. 400-401.
March, Advanced Organic Chemistry, Third Edition, pp. 310-317 (John Wiley & Sons, New York).
McGraw-Hill Dictionary of Scientific and Technical Terms, Fourth Edition, pp. 187 and 1392 (McGraw-Hill Book Co., New York).
Ortuno et al., Tetrahedron, vol. 43, No. 19, pp. 4497-4506 (1987).
Hoppe et al., Angew. Chem. Int. Ed. Engl., vol. 28, No. 1, pp. 69-71 (1989).
Shibagaki et al., Chemistry Letters, pp. 307-310 (1990).
Mori et al., Carbohydrate Research, vol. 129, pp. 73-86 (1984).
Marshall et al., J. Org. Chem., vol. 49, pp. 747-753 (1984).
Ebata et al., Heterocycles, vol. 31, No. 9, pp. 1585-1588 (1990).

Affiliated with

Also associated with

Rating

Method of preparing trans-3,4-disubstituted-.gamma.-lactones does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of preparing trans-3,4-disubstituted-.gamma.-lactones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of preparing trans-3,4-disubstituted-.gamma.-lactones will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1816194