CAS 1225277-47-3

1,3-Diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-myo-inositol

Description:

1,3-Diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-myo-inositol is a complex organic compound characterized by multiple azido groups, which are known for their reactivity and potential applications in click chemistry. The presence of a D-myo-inositol backbone suggests that it may exhibit biological activity, possibly interacting with cellular pathways or serving as a precursor for further chemical modifications. The compound's stereochemistry, indicated by the (2S,3R) configuration, implies specific spatial arrangements that can influence its reactivity and interactions with biological targets. Additionally, the presence of various functional groups, such as azido, methylamino, and pyran structures, contributes to its potential versatility in synthetic chemistry and medicinal applications. Overall, this compound represents a significant interest in the fields of organic synthesis and medicinal chemistry due to its unique structural features and potential utility in drug development or as a biochemical probe.

Formula: C₁₉H₂₉N₁₃O₇

InChI: InChI=1S/C19H29N13O7/c1-19(35)7-36-18(13(34)16(19)24-2)39-15-11(28-32-23)5-10(27-31-22)14(12(15)33)38-17-9(26-30-21)4-3-8(37-17)6-25-29-20/h3,9-18,24,33-35H,4-7H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1

InChI key: InChIKey=KJCLXKZNJQKRQN-YFMIWBNJSA-N

SMILES: O([C@@H]1[C@@H](N=[N+]=[N-])C[C@@H](N=[N+]=[N-])[C@H](O[C@@H]2[C@H](O)[C@@H](NC)[C@@](C)(O)CO2)[C@H]1O)[C@@H]3[C@H](N=[N+]=[N-])CC=C(CN=[N+]=[N-])O3

Synonyms:

• 1,3-Diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-myo-inositol
• D-myo-Inositol, 1,3-diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-

1,3-Diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-myo-inositol

Controlled Product

CAS: 1225277-47-3

Applications 1,3-Diazido-4-O-[(2S,3R)-3-azido-6-(azidomethyl)-3,4-dihydro-2H-pyran-2-yl]-1,2,3-trideoxy-6-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]-D-myo-inositol is an intermediate used in the synthesis of O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-D-streptamine (A604395), which is an impurity of Tobramycin (T524000), a single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius.
References Koch, K.F., et al.: Antimicrob. Agents Chemother., 309 (1970); Welles, J.S., et al.: Toxicol. Appl. Pharmacol., 22, 332 (1972); Dash, A.K., et al.: Anal. Profiles Drug Subs. Excip., 24, 579 (1996)

Formula: C₁₉H₂₉N₁₃O₇

Color and Shape: Neat

Molecular weight: 551.516

Ref: TR-D417558