N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide

• ChemBase ID: 76109
• Molecular Formular: C18H25NO6
• Molecular Mass: 351.3942
• Monoisotopic Mass: 351.16818753
• SMILES: CC(=O)N[C@@H]1[C@@H](O)[C@@H]2OC(C)(C)OC[C@H]2O[C@@H]1OCc1ccccc1
• Canonical SMILES: CC(=O)N[C@H]1[C@@H](OCc2ccccc2)O[C@H]2[C@H]([C@@H]1O)OC(OC2)(C)C
• InChI: InChI=1S/C18H25NO6/c1-11(20)19-14-15(21)16-13(10-23-18(2,3)25-16)24-17(14)22-9-12-7-5-4-6-8-12/h4-8,13-17,21H,9-10H2,1-3H3,(H,19,20)/t13-,14-,15-,16-,17+/m1/s1
• InChIKey: BBFJZZWRXVVKEC-HHARLNAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• IUPAC Traditional name: N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: Benzyl-2-acetamido-2-deoxy-4,6-O-isopropylidene-alpha-D-glucopyranoside

Database IDs

• MDL Number: MFCD00269925
• PubChem SID: 162041024
• PubChem CID: 11900052

CALCULATED PROPERTIES

• Acid pKa: 12.505089
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.8494496
• LogD (pH = 7.4): 0.8494468
• Log P: 0.8494498
• Molar Refractivity: 88.5955 cm^3
• Polarizability: 35.630535 Å^3
• Polar Surface Area: 86.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 138°C; 173.5-175.5°C

DETAILS

Apollo Scientific Ltd - OR1257T

An intermediate in the synthesis of Lipid A, which is said to be responsible for most of the biological activities of the lipopolysaccharide of gm-negative bacteria.