Home > Name List By b > Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-gluco...

CAS No 17650-86-1 , Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-

  • Name: Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-
  • Synonyms: NSC 5340; Benzamide,4-[(2-amino-3-hydroxy-2-methyl-1-oxopropyl)amino]-N-[1-[5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-,[2R-[2a(S*),5b,6a]]-;Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-; Sacromycin; Hydracrylanilide,2-amino-4'-[[1,2-dihydro-2-oxo-1-[2,3,6-trideoxy-4-O-[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]-b-D-erythro-hexopyranosyl]-4-pyrimidinyl]carbamoyl]-2-methyl-(7CI,8CI);Amicetin(6CI); Allomycin;
  • CAS Registry Number:
  • Density: 1.46g/cm3
  • Refractive index: 1.651
  • Safety Statements: Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Molecular Weight: 618.77
  • InChI: InChI=1/C29H42N6O9/c1-15-19(44-26-24(38)23(37)22(34(4)5)16(2)43-26)10-11-21(42-15)35-13-12-20(33-28(35)41)32-25(39)17-6-8-18(9-7-17)31-27(40)29(3,30)14-36/h6-9,12-13,15-16,19,21-24,26,36-38H,10-11,14,30H2,1-5H3,(H,31,40)(H,32,33,39,41)
  • Molecular Formula: C29H42 N6 O9
  • Molecular Structure:CAS No:17650-86-1 Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-

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References of Benzamide,4-[[(2S)-2-amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]-
Title: Amicetin
CAS Registry Number: 17650-86-1
CAS Name: 4-[[(2S)-2-Amino-3-hydroxy-2-methyl-1-oxopropyl]amino]-N-[1-[(2R,5S,6R)-5-[[4,6-dideoxy-4-(dimethylamino)-a-D-glucopyranosyl]oxy]tetrahydro-6-methyl-2H-pyran-2-yl]-1,2-dihydro-2-oxo-4-pyrimidinyl]benzamide
Molecular Formula: C29H42N6O9
Molecular Weight: 618.68
Percent Composition: C 56.30%, H 6.84%, N 13.58%, O 23.27%
Literature References: Antibiotic substance produced by Streptomyces vinaceus-drappus isolated from soil near Kalamazoo, Mich.: C. DeBoer et al., J. Am. Chem. Soc. 75, 499 (1953); J. W. Hinman et al., ibid. 5864; McKormich, Hoehn, Antibiot. Chemother. 3, 718 (1953). Chemistry: E. H. Flynn et al., J. Am. Chem. Soc. 75, 5867 (1953). Structural studies: C. L. Stevens et al., J. Org. Chem. 27, 2991 (1962). Configuration: S. Hanessian, T. H. Haskell, Tetrahedron Lett. 5, 2451 (1964). Inhibition of protein synthesis: A. Bloch, C. Coutsogeorgopoulos, Biochemistry 5, 3345 (1966). Binding to 23S rRNA as mechanism of inhibition of peptide bond formation: I. G. Leviev et al., EMBO J. 13, 1682 (1994).
Properties: Colorless granular crystals, mp 244-245°. pKa = 10.4, 7.0. [a]D24 +116.5° (c = 0.5 in 0.1N HCl). uv max in water: 305 nm (E1%1cm 465); in 0.1N HCl: 316 nm (E1%1cm 433); in 0.1N NaOH: 322 nm (E1%1cm 470). Soly in water at 25° = 2 mg/ml. Slightly sol in common organic solvents. LD50 of citrate complex, pH 6 (mg/kg) in mice: ~90 i.v., 600-700 s.c.; in rats: ~200 i.v., ~600 s.c. (DeBoer).
Melting point: mp 244-245°
pKa: pKa = 10.4, 7.0
Optical Rotation: [a]D24 +116.5° (c = 0.5 in 0.1N HCl)
Absorption maximum: uv max in water: 305 nm (E1%1cm 465); in 0.1N HCl: 316 nm (E1%1cm 433); in 0.1N NaOH: 322 nm (E1%1cm 470)
Toxicity data: LD50 of citrate complex, pH 6 (mg/kg) in mice: ~90 i.v., 600-700 s.c.; in rats: ~200 i.v., ~600 s.c. (DeBoer)