methyl (2R,4R,5S)-4-(acetyloxy)-5-acetamido-2-(ethylsulfanyl)-3-(phenylsulfanyl)-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate

• ChemBase ID: 159121
• Molecular Formular: C28H37NO12S2
• Molecular Mass: 643.72288
• Monoisotopic Mass: 643.17571763
• SMILES: C1([C@@H]([C@@H](C([C@](O1)(SCC)C(=O)OC)Sc1ccccc1)OC(=O)C)NC(=O)C)[C@@H]([C@H](COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CCS[C@]1(OC([C@@H]([C@@H](OC(=O)C)COC(=O)C)OC(=O)C)[C@@H]([C@@H](C1Sc1ccccc1)OC(=O)C)NC(=O)C)C(=O)OC
• InChI: InChI=1S/C28H37NO12S2/c1-8-42-28(27(35)36-7)26(43-20-12-10-9-11-13-20)25(40-19(6)34)22(29-15(2)30)24(41-28)23(39-18(5)33)21(38-17(4)32)14-37-16(3)31/h9-13,21-26H,8,14H2,1-7H3,(H,29,30)/t21-,22-,23+,24?,25+,26?,28-/m0/s1
• InChIKey: CBZNDOIJCAZHDR-NBYMNXNUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,4R,5S)-4-(acetyloxy)-5-acetamido-2-(ethylsulfanyl)-3-(phenylsulfanyl)-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,4R,5S)-4-(acetyloxy)-5-acetamido-2-(ethylsulfanyl)-3-(phenylsulfanyl)-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: 5-(Acetylamino)-5-deoxy-3-S-phenyl-2-S-ethyl-2,3-dithio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Database IDs

• PubChem SID: 162253256
• PubChem CID: 71312814

CALCULATED PROPERTIES

• Acid pKa: 12.909778
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.9550235
• LogD (pH = 7.4): 1.9550229
• Log P: 1.9550241
• Molar Refractivity: 152.8224 cm^3
• Polarizability: 62.207733 Å^3
• Polar Surface Area: 169.83 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A168215

An intermediate in the production of STn Epitope