(1R,2S,4S,7S,9R,12R)-7-methoxy-4,12-diphenyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane

• ChemBase ID: 173543
• Molecular Formular: C21H22O6
• Molecular Mass: 370.39578
• Monoisotopic Mass: 370.14163842
• SMILES: [C@H]12[C@H]3C([C@H](O[C@@H]1CO[C@H](O2)c1ccccc1)OC)O[C@H](O3)c1ccccc1
• Canonical SMILES: CO[C@H]1O[C@@H]2CO[C@H](O[C@H]2[C@H]2C1O[C@H](O2)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C21H22O6/c1-22-21-18-17(26-20(27-18)14-10-6-3-7-11-14)16-15(24-21)12-23-19(25-16)13-8-4-2-5-9-13/h2-11,15-21H,12H2,1H3/t15-,16-,17+,18?,19-,20+,21+/m1/s1
• InChIKey: VGLOFWHLPMVSBF-JNXOPKTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,4S,7S,9R,12R)-7-methoxy-4,12-diphenyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.0^2,^6]tridecane
• IUPAC Traditional name: (1R,2S,4S,7S,9R,12R)-7-methoxy-4,12-diphenyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.0^2,^6]tridecane
• Synonyms: Methyl 2,3:4,6-Bis-O-(phenylmethylene)-α-D-mannopyranoside; NSC 266498; Methyl 2,3:4,6-Di-O-benzylidene-α-D-mannopryanoside

Database IDs

• CAS Number: 4148-71-4
• PubChem SID: 164229453
• PubChem CID: 71750292

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 4.0407457
• LogD (pH = 7.4): 4.0407457
• Log P: 4.0407457
• Molar Refractivity: 94.4418 cm^3
• Polarizability: 38.47107 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Crystalline Solid
• Melting Point: 182-184°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M300110

Methyl 2,3:4,6-Di-O-benzylidene-α-D-mannopryanoside is used in the synthesis of a key intermediate of (+)-ajmalicine from carbohydrates and tryptamine.

REFERENCES

• Horton, D., et al.: Carbohydr. Res., 44, 227 (1975)