Title: Mycarose
CAS Registry Number: 6032-92-4
CAS Name: 2,6-Dideoxy-3-C-methyl-L-ribo-hexose
Additional Names: 2,6-didesoxy-3-C-methyl-L-ribo-hexose; 2-(4,5-cis)-trihydroxy-4,6-dimethyltetrahydropyran
Molecular Formula: C7H14O4
Molecular Weight: 162.18
Percent Composition: C 51.84%, H 8.70%, O 39.46%
Literature 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).
Derivative Type: DL-Form
Properties: Crystals from acetone + petr ether, mp 110-111°.
Melting point: mp 110-111°
Derivative Type: L-Form
Properties: Needles from boiling acetone + chloroform, mp 128.5-130.5°. [a]D25 -31.1° (c = 4). Sol in water. Exhibits only end absorption in the ultraviolet.
Melting point: mp 128.5-130.5°
Optical Rotation: [a]D25 -31.1° (c = 4)
Derivative Type: 3-O-Methylmycarose
Trademarks: Cladinose
Molecular Formula: C8H16O4
Molecular Weight: 176.21
Percent Composition: C 54.53%, H 9.15%, O 36.32%
Properties: Constituent of erythromycin A and B. Liquid, bp0.25 at bath temp 120-132°. [a]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.
Boiling point: bp0.25 at bath temp 120-132°
Optical Rotation: [a]D25 -23.1° (c = 2.6 in water)
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