6318. Mycarose

Nomenclature

CAS number: 6032-92-4
2,6-Dideoxy-3-C-methyl-l-ribo-hexose; 2,6-didesoxy-3-C-methyl-l-ribo-hexose; 2-(4,5-cis)-trihydroxy-4,6-dimethyltetrahydropyran.
C7H14O4; mol wt 162.18.
C 51.84%, H 8.70%, O 39.46%.

Description and references

Constituent of the macrolides carbomycin A and B, spiramycin A, B and C and tylosin: Woodward, Angew. Chem. 69, 50 (1957); Paul, Tchelitcheff, Bull. Soc. Chim. Fr. 1957, 443; 1960, 150; Hamill et al., Antibiot. Chemother. 11, 328 (1961). Part of carbomycin molecule: Regna et al., J. Am. Chem. Soc. 75, 4625 (1953). Stereochemistry: Grisebach, Hofheinz, Angew. Chem. 74, 499 (1962); Foster et al., Proc. Chem. Soc. London 1962, 254; Hofheinz et al., Tetrahedron 18, 1265 (1962). Synthesis of dl-mycarose: Korte et al., ibid. 1257; Grisebach et al., Ber. 96, 1823 (1963). Synthesis of l-mycarose: Lemal et al., Tetrahedron 18, 1275 (1962); Koto et al., Bull. Chem. Soc. Jpn. 45, 532 (1972). Synthesis of d-mycarose: Flaherty et al., J. Chem. Soc. C 1966, 398. Isoln from aureolic acid: Berlin et al., Khim. Prir. Soedin. 8, 535 (1972), C.A. 78, 4432a (1973).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from acetone + petr ether, mp 110-111°.

Derivative

l-Form.

Properties

Needles from boiling acetone + chloroform, mp 128.5-130.5°. [α]D25 -31.1° (c = 4). Sol in water. Exhibits only end absorption in the ultraviolet.

Derivative

3-O-Methylmycarose.

Nomenclature

Cladinose.
C8H16O4; mol wt 176.21.
C 54.53%, H 9.15%, O 36.32%.

Properties

Constituent of erythromycin A and B. Liquid, bp0.25 at bath temp 120-132°. [α]D25 -23.1° (c = 2.6 in water). Sol in water, alcohol, acetone, ether, benzene, chloroform, carbon tetrachloride; slightly sol in petr ether. Dec by strong acids.