[(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-acetamido-6-(ethylsulfanyl)oxan-2-yl]methyl acetate

• ChemBase ID: 168776
• Molecular Formular: C16H25NO8S
• Molecular Mass: 391.4366
• Monoisotopic Mass: 391.13008777
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)SCC)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CCS[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1NC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H25NO8S/c1-6-26-16-13(17-8(2)18)15(24-11(5)21)14(23-10(4)20)12(25-16)7-22-9(3)19/h12-16H,6-7H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16+/m1/s1
• InChIKey: BHOPGYBLLSFEGH-QCODTGAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-acetamido-6-(ethylsulfanyl)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-acetamido-6-(ethylsulfanyl)oxan-2-yl]methyl acetate
• Synonyms: Ethyl 2-(Acetylamino)-2-deoxy-1-thio-β-D-glucopyranoside 3,4,6-Triacetate; Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thioglucopyranoside

Database IDs

• CAS Number: 4239-72-9
• PubChem SID: 162262908
• PubChem CID: 14160908

CALCULATED PROPERTIES

• Acid pKa: 12.708443
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.29005077
• LogD (pH = 7.4): -0.29005238
• Log P: -0.29005048
• Molar Refractivity: 90.1484 cm^3
• Polarizability: 36.963608 Å^3
• Polar Surface Area: 117.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid, stench
• Melting Point: 175-177°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E927150

A reagent for the preparation of GlcNAc glycosides.

REFERENCES

• Peter, T., et al.: Liebigs Ann. Chem., 237 (1991)