tert-butyl N-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)carbamate

• ChemBase ID: 162569
• Molecular Formular: C21H28NO6P
• Molecular Mass: 421.423881
• Monoisotopic Mass: 421.16542425
• SMILES: N(CCOP(=O)(OCc1ccccc1)OCc1ccccc1)C(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)NCCOP(=O)(OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C21H28NO6P/c1-21(2,3)28-20(23)22-14-15-25-29(24,26-16-18-10-6-4-7-11-18)27-17-19-12-8-5-9-13-19/h4-13H,14-17H2,1-3H3,(H,22,23)
• InChIKey: RVSMWJQWFJMFMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)carbamate
• IUPAC Traditional name: tert-butyl N-{2-[(dibenzyloxyphosphoryl)oxy]ethyl}carbamate
• Synonyms: 8-Phenyl-6-(phenylmethoxy)-5,7-dioxa-2-aza-6-phosphaoctanoic Acid 1,1-Dimethylethyl Ester 6-Oxide; Boc-ethanolamine Dibenzylphosphate

Database IDs

• CAS Number: 1076199-25-1
• PubChem SID: 162256704
• PubChem CID: 29974624

CALCULATED PROPERTIES

• Acid pKa: 14.569513
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.2578382
• LogD (pH = 7.4): 4.2578382
• Log P: 4.2578382
• Molar Refractivity: 110.1468 cm^3
• Polarizability: 43.776524 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B649500

An intermediate of 1-Deoxy-D-xylulose 5-phosphate (DXP), as inhibitor of E. coli methylerythritol phosphate synthase.

REFERENCES

• Flesch, G., et al.: Eur. J. Biochem., 175, 405 (1988)
• Rohmer, M., et al.: Biochem. J., et al.: 295, 517 (1988)
• Proteau, P.J., et al.: Bioorg. Chem., 32, 483 (1988)