(3aS,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-methoxy-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran

• ChemBase ID: 178913
• Molecular Formular: C30H34O7
• Molecular Mass: 506.58676
• Monoisotopic Mass: 506.23045343
• SMILES: [C@@H]12O[C@H]([C@H]([C@@H]([C@@H]1OC(O2)(C)OC)OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• Canonical SMILES: COC1(C)O[C@H]2[C@@H](O1)[C@@H](OCc1ccccc1)[C@@H]([C@@H](O2)COCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C30H34O7/c1-30(31-2)36-28-27(34-20-24-16-10-5-11-17-24)26(33-19-23-14-8-4-9-15-23)25(35-29(28)37-30)21-32-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3/t25-,26-,27+,28+,29+,30?/m1/s1
• InChIKey: SCDVHQXHQOSKCS-LGPOITBMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-methoxy-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran
• IUPAC Traditional name: (3aS,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-methoxy-2-methyl-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran
• Synonyms: 1,2-O-(1-Methoxyethylidene)-3,4,6-tris-O-(phenylmethyl)-β-D-mannopyranose; 3,4,6-Tri-O-benzyl-β-D-mannopyranose 1,2-(Methyl Orthoacetate)

Database IDs

• CAS Number: 16697-49-7
• PubChem SID: 164234823
• PubChem CID: 11092390

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 6.2015066
• LogD (pH = 7.4): 6.2015066
• Log P: 6.2015066
• Molar Refractivity: 137.6806 cm^3
• Polarizability: 54.99396 Å^3
• Polar Surface Area: 64.61 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 74-76°C

Safety Information

• Storage Condition: Refrigerator

REFERENCES

• Marino-Albernas, J., et al.: J. Med. Chem., 39, 3241 (1996)
• Chakraborty, N., et al.: Bioorg. Med. Chem., 13, 6732 (1996)
• Collot, M., et al.: J. Med. Chem., 51, 6201 (1996)