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

• ChemBase ID: 161361
• Molecular Formular: C18H25NO6
• Molecular Mass: 351.3942
• Monoisotopic Mass: 351.16818753
• SMILES: [C@H]1([C@@H]([C@@H](O[C@H]2[C@H]1OC(OC2)(C)C)OCc1ccccc1)NC(=O)C)O
• 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-WRQOLXDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,6R,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,6R,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-β-D-glucopyranoside,BADIG; Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Database IDs

• CAS Number: 50605-12-4
• PubChem SID: 162255496
• PubChem CID: 7370993

CALCULATED PROPERTIES

• 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
• Acid pKa: 12.505089
• H Acceptors: 6
• H Donor: 2

PROPERTIES

Physical Property

• Melting Point: 173.5-175.5°C

DETAILS

Toronto Research Chemicals - B212570

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

REFERENCES

• Ishida, H., et al.: Agric. Biol. Chem., 53, 1269 (1989)