(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-one

• ChemBase ID: 178250
• Molecular Formular: C34H34O6
• Molecular Mass: 538.63016
• Monoisotopic Mass: 538.23553881
• SMILES: C1(=O)O[C@H]([C@@H]([C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• Canonical SMILES: O=C1O[C@@H](COCc2ccccc2)[C@@H]([C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C34H34O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-33H,21-25H2/t30-,31+,32+,33-/m1/s1
• InChIKey: BUBVLQDEIIUIQG-JDIHBLRXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-one
• IUPAC Traditional name: (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-one
• Synonyms: 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactonic Acid δ-Lactone; 2,3,4,6-Tetra-O-benzyl-D-galactono-1,5-lactone

Database IDs

• CAS Number: 82598-84-3
• PubChem SID: 164234160
• PubChem CID: 11060569

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 6.7251253
• LogD (pH = 7.4): 6.7251253
• Log P: 6.7251253
• Molar Refractivity: 152.234 cm^3
• Polarizability: 60.32135 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T284950

It is used in peptide coupling reactions.

REFERENCES

• Varki, A., et al.: Glycobiology, 3, 97 (1993)
• Liu, J., et al.: J. Med. Chem., 41, 1382 (1993)