(2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7,8-bis(prop-2-en-1-yloxy)-hexahydro-2H-pyrano[3,2-d][1,3]dioxine

• ChemBase ID: 173535
• Molecular Formular: C20H26O6
• Molecular Mass: 362.41684
• Monoisotopic Mass: 362.17293855
• SMILES: [C@H]12[C@@H]([C@@H]([C@H](O[C@@H]1CO[C@H](O2)c1ccccc1)OC)OCC=C)OCC=C
• Canonical SMILES: C=CCO[C@H]1[C@@H]2O[C@@H](OC[C@H]2O[C@@H]([C@H]1OCC=C)OC)c1ccccc1
• InChI: InChI=1S/C20H26O6/c1-4-11-22-17-16-15(25-20(21-3)18(17)23-12-5-2)13-24-19(26-16)14-9-7-6-8-10-14/h4-10,15-20H,1-2,11-13H2,3H3/t15-,16-,17+,18+,19-,20+/m1/s1
• InChIKey: FMKYMGOFTWEBLP-JWLCQNFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7,8-bis(prop-2-en-1-yloxy)-hexahydro-2H-pyrano[3,2-d][1,3]dioxine
• IUPAC Traditional name: (2R,4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7,8-bis(prop-2-en-1-yloxy)-hexahydro-2H-pyrano[3,2-d][1,3]dioxine
• Synonyms: Methyl 4,6-O-(Phenylmethylene)-2,3-di-O-2-propenyl-α-D-mannopyranoside; Methyl 2,3-Di-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside

Database IDs

• CAS Number: 359437-00-6
• PubChem SID: 164229445
• PubChem CID: 71750289

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.6244192
• LogD (pH = 7.4): 3.6244192
• Log P: 3.6244192
• Molar Refractivity: 95.386 cm^3
• Polarizability: 38.332825 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Clear Oil with Greenish Tinge

DETAILS

Toronto Research Chemicals - M299200

Methyl 2,3-Di-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside is used in the synthesis of manno crown ethers.

REFERENCES

• Pettman, R.B., et al.: Tetrahedr. Lett., 5, 461 (1979)