(2S,3R,4S,5S,6R)-2-{[(1R,5R,7E,9E,11R,12R,14R,16S,18S)-16-[(tert-butyldimethylsilyl)oxy]-18-methoxy-5,12-dimethyl-11-{[(5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy}-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy}-5-{[(2S,4R,5S,6S)-5-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-6-methyloxan-3-yl acetate

• ChemBase ID: 159184
• Molecular Formular: C56H102N2O15Si2
• Molecular Mass: 1099.58448
• Monoisotopic Mass: 1098.68187364
• SMILES: O1C(=O)C[C@@H]2[C@@H](C([C@H](C[C@H]([C@H](/C=C/C=C/C[C@H]1C)OC1CC[C@@H]([C@H](O1)C)NC)C)C[C@@H](O2)O[Si](C(C)(C)C)(C)C)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C)O[C@@H]1O[C@@H]([C@@H]([C@@](C1)(O)C)O[Si](C(C)(C)C)(C)C)C)N(C)C)OC(=O)C)OC
• Canonical SMILES: CO[C@H]1[C@H]2CC(=O)O[C@H](C)C/C=C/C=C/[C@@H]([C@@H](C[C@@H](C1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1OC(=O)C)N(C)C)O[C@@H]1O[C@H](C)[C@@H]([C@](C1)(C)O)O[Si](C(C)(C)C)(C)C)C[C@@H](O2)O[Si](C(C)(C)C)(C)C)C)OC1CC[C@@H]([C@H](O1)C)NC
• InChI: InChI=1S/C56H102N2O15Si2/c1-33-29-39-30-45(72-74(18,19)54(7,8)9)69-42(31-43(60)63-34(2)25-23-22-24-26-41(33)68-44-28-27-40(57-14)35(3)64-44)50(62-17)49(39)71-53-51(67-38(6)59)47(58(15)16)48(36(4)66-53)70-46-32-56(13,61)52(37(5)65-46)73-75(20,21)55(10,11)12/h22-24,26,33-37,39-42,44-53,57,61H,25,27-32H2,1-21H3/b23-22+,26-24+/t33-,34-,35-,36-,37+,39-,40+,41+,42-,44?,45+,46+,47+,48-,49?,50+,51-,52+,53+,56-/m1/s1
• InChIKey: COTXJGFUQLISCR-JMPRYJIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(1R,5R,7E,9E,11R,12R,14R,16S,18S)-16-[(tert-butyldimethylsilyl)oxy]-18-methoxy-5,12-dimethyl-11-{[(5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy}-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy}-5-{[(2S,4R,5S,6S)-5-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-6-methyloxan-3-yl acetate
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-2-{[(1R,5R,7E,9E,11R,12R,14R,16S,18S)-16-[(tert-butyldimethylsilyl)oxy]-18-methoxy-5,12-dimethyl-11-{[(5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy}-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy}-5-{[(2S,4R,5S,6S)-5-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-6-methyloxan-3-yl acetate
• Synonyms: 2'-O-Acetyl-4''-O-tert-butyldimethylsilyl-4'''-de-N-methylspiramycin I 3,18-(O-tert-Butyldimethylsilyl)acetal; 9(2R,5S,6R)]-18-Deoxo-3-deoxy-4B-O-[(1,1-dimethylethyl)dimethylsilyl]-18-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,18-epoxy-9-O-[tetrahydro-6-methyl-5-(methylamino)-2H-pyran-2-yl]-leucomycin V 2B-Acetate

Database IDs

• CAS Number: 96405-33-3
• PubChem SID: 162253319
• PubChem CID: 71312847

CALCULATED PROPERTIES

• Acid pKa: 13.840353
• H Acceptors: 15
• H Donor: 2
• LogD (pH = 5.5): 1.2292649
• LogD (pH = 7.4): 4.02767
• Log P: 7.3531
• Molar Refractivity: 281.6177 cm^3
• Polarizability: 117.81036 Å^3
• Polar Surface Area: 180.4 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A171180

Spiramycin intermediate.

REFERENCES

• Sous, H., et al.: Arzneim.-Forsch., 8, 386 (1958)
• Mitscher, et al.: J. Antibiot., 26, 55 (1973)