(6S,8R,8aS)-6-(benzyloxy)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol

• ChemBase ID: 161422
• Molecular Formular: C20H22O6
• Molecular Mass: 358.38508
• Monoisotopic Mass: 358.14163842
• SMILES: [C@H]1(C([C@H](OC2[C@H]1OC(OC2)c1ccccc1)OCc1ccccc1)O)O
• Canonical SMILES: O[C@H]1[C@@H]2OC(OCC2O[C@@H](C1O)OCc1ccccc1)c1ccccc1
• InChI: InChI=1S/C20H22O6/c21-16-17(22)20(23-11-13-7-3-1-4-8-13)25-15-12-24-19(26-18(15)16)14-9-5-2-6-10-14/h1-10,15-22H,11-12H2/t15?,16-,17?,18-,19?,20+/m1/s1
• InChIKey: LEJLVYJUXVHIJN-DXGZHBHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S,8R,8aS)-6-(benzyloxy)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• IUPAC Traditional name: (6S,8R,8aS)-6-(benzyloxy)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• Synonyms: Phenylmethyl 4,6-O-(Phenylmethylene)-α-D-mannopyranoside; Benzyl 4,6-O-Benzylidene-α-D-mannopyranoside

Database IDs

• CAS Number: 40983-94-6
• PubChem SID: 162255557
• PubChem CID: 71313777

CALCULATED PROPERTIES

• Acid pKa: 12.275489
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.6001396
• LogD (pH = 7.4): 2.600134
• Log P: 2.6001396
• Molar Refractivity: 92.1708 cm^3
• Polarizability: 37.218365 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 147-149°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B232500

Used in the synthesis of some O-D-xylosyl-D-mannoses and their derivatives.

REFERENCES

• Lee, R.T., et al.: Carbohydrate Res., 67, 389 (1978)