methyl (2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoate

• ChemBase ID: 161383
• Molecular Formular: C26H31NO8
• Molecular Mass: 485.52624
• Monoisotopic Mass: 485.20496696
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]2[C@H]1OC(OC2)c1ccccc1)OCc1ccccc1)NC(=O)C)O[C@@H](C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H](O[C@H]1[C@@H]2OC(OC[C@H]2O[C@@H]([C@H]1NC(=O)C)OCc1ccccc1)c1ccccc1)C
• InChI: InChI=1S/C26H31NO8/c1-16(24(29)30-3)33-23-21(27-17(2)28)26(31-14-18-10-6-4-7-11-18)34-20-15-32-25(35-22(20)23)19-12-8-5-9-13-19/h4-13,16,20-23,25-26H,14-15H2,1-3H3,(H,27,28)/t16-,20+,21+,22+,23+,25?,26-/m0/s1
• InChIKey: ZDYOCWILIJFUOR-BCHDKMROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoate
• IUPAC Traditional name: methyl (2S)-2-{[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoate
• Synonyms: N-Acetyl-1-O-(phenylmethyl)-4,6-O-(phenylmethylene)-α-isomuramic Acid Methyl Ester; 2-Acetamido-4,6-O-benzylidene-3-O-(L-1-carboxyethyl)-2-deoxy-α-D-glucopyranoside Benzyl Methyl Ester; Benzyl N-Acetyl-4,6-O-benzylidene-α-isomuramic Acid Methyl Ester

Database IDs

• CAS Number: 104371-52-0
• PubChem SID: 162255518
• PubChem CID: 71313761

CALCULATED PROPERTIES

• Acid pKa: 12.477998
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 3.1478722
• LogD (pH = 7.4): 3.1478693
• Log P: 3.1478727
• Molar Refractivity: 123.3709 cm^3
• Polarizability: 49.73093 Å^3
• Polar Surface Area: 101.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - B223275

A derivative of isomuramic acid.

REFERENCES

• Gross, P.: Liebigs Ann. Chem. 1, 37 (1986)