(4aR,6R,7S,8S,8aR)-7,8-bis(benzyloxy)-6-(ethanesulfinyl)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine

• ChemBase ID: 168494
• Molecular Formular: C29H32O6S
• Molecular Mass: 508.62578
• Monoisotopic Mass: 508.19195974
• SMILES: [C@H]12[C@@H]([C@@H]([C@H](O[C@@H]1COC(O2)c1ccccc1)S(=O)CC)OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: CCS(=O)[C@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)c1ccccc1
• InChI: InChI=1S/C29H32O6S/c1-2-36(30)29-27(32-19-22-14-8-4-9-15-22)26(31-18-21-12-6-3-7-13-21)25-24(34-29)20-33-28(35-25)23-16-10-5-11-17-23/h3-17,24-29H,2,18-20H2,1H3/t24-,25-,26+,27+,28?,29-,36?/m1/s1
• InChIKey: HOPJJYXGUGPOFD-FHPUVLEPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7S,8S,8aR)-7,8-bis(benzyloxy)-6-(ethanesulfinyl)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine
• IUPAC Traditional name: (4aR,6R,7S,8S,8aR)-7,8-bis(benzyloxy)-6-(ethanesulfinyl)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine
• Synonyms: 1-Deoxy-1-(ethylsulfinyl)-2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-α-D-mannopyranose; Ethyl 2,3-Di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside S-Oxide

Database IDs

• CAS Number: 188357-34-8
• PubChem SID: 162262626
• PubChem CID: 71316562

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 4.815121
• LogD (pH = 7.4): 4.815121
• Log P: 4.815121
• Molar Refractivity: 138.7295 cm^3
• Polarizability: 55.376347 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 123-124°C

DETAILS

Toronto Research Chemicals - E915775

Used in direct synthesis of β-mannopyranosides by the sulfoxide method.

REFERENCES

• Srivastava, V., et al.: Carbohydr. Res., 79, C13 (1980)
• Liang, R., et al.: Science, 274, 1520 (1980)