methyl (2R)-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: 161382
• 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+/m1/s1
• InChIKey: ZDYOCWILIJFUOR-GORWESQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-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 (2R)-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-muramic Acid Methyl Ester; [3(R)]-Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-(2-methoxy-1-methyl-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-glucopyranoside; Benzyl N-Acetyl-4,6-O-benzylidene-α-D-muramic Acid Methyl Ester

Database IDs

• CAS Number: 104371-51-9
• PubChem SID: 162255517
• PubChem CID: 71313760

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; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 205-206°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B223270

The N-acetyl derivative of muramic acid is an amino sugar found in peptidoglycan, the main skeletal component of both Gram positive and Gram negative bacterial cell wall.

REFERENCES

• J. Biol. Chem., 194, 885, 1952; Ann. NY Acad. Sci., 235, 29-51 (1974)
• J. Am. Chem. Soc., 28, 2983 (1963)