[(3aS,5R,6R,7S,7aS)-2-{[(3aS,5R,6R,7S,7aS)-5-({[(3aR,5S,6S,7R,7aR)-6,7-bis(acetyloxy)-5-[(acetyloxy)methyl]-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy}methyl)-6-(acetyloxy)-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-7-yl]oxy}-6,7-bis(acetyloxy)-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate

• ChemBase ID: 159248
• Molecular Formular: C38H52O25
• Molecular Mass: 908.80448
• Monoisotopic Mass: 908.27976716
• SMILES: [C@@H]1([C@@H]([C@H]2[C@@H](O[C@H]1COC1(O[C@@H]3[C@@H]([C@H]([C@H](O[C@@H]3O1)COC(=O)C)OC(=O)C)OC(=O)C)C)OC(O2)C)OC1(O[C@@H]2[C@@H](O[C@H]([C@H]([C@@H]2OC(=O)C)OC(=O)C)COC(=O)C)O1)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H]2OC(O[C@@H]2[C@@H]([C@H]1OC(=O)C)OC(=O)C)(C)OC[C@@H]1O[C@H]2OC(O[C@H]2[C@H]([C@@H]1OC(=O)C)OC1(C)O[C@@H]2[C@H](O1)O[C@H]([C@H]([C@@H]2OC(=O)C)OC(=O)C)COC(=O)C)C
• InChI: InChI=1S/C38H52O25/c1-14(39)46-11-22-25(49-16(3)41)28(52-19(6)44)32-35(57-22)62-37(9,60-32)48-13-24-27(51-18(5)43)30(31-34(56-24)55-21(8)54-31)59-38(10)61-33-29(53-20(7)45)26(50-17(4)42)23(12-47-15(2)40)58-36(33)63-38/h21-36H,11-13H2,1-10H3/t21?,22-,23+,24+,25-,26+,27+,28+,29-,30-,31-,32+,33-,34+,35+,36-,37?,38?/m0/s1
• InChIKey: AOXHPNMURYCURT-MSJQPOHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aS,5R,6R,7S,7aS)-2-{[(3aS,5R,6R,7S,7aS)-5-({[(3aR,5S,6S,7R,7aR)-6,7-bis(acetyloxy)-5-[(acetyloxy)methyl]-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy}methyl)-6-(acetyloxy)-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-7-yl]oxy}-6,7-bis(acetyloxy)-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• IUPAC Traditional name: [(3aS,5R,6R,7S,7aS)-2-{[(3aS,5R,6R,7S,7aS)-5-({[(3aR,5S,6S,7R,7aR)-6,7-bis(acetyloxy)-5-[(acetyloxy)methyl]-2-methyl-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-yl]oxy}methyl)-6-(acetyloxy)-2-methyl-hexahydro-[1,3]dioxolo[4,5-b]pyran-7-yl]oxy}-6,7-bis(acetyloxy)-2-methyl-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl acetate
• Synonyms: O-3,4,6-Tri-O-acetyl-β-D-mannopyranosylethylidyne-(1-23)-O-[3,4,6-tri-O-acetyl-β-D-mannopyranosylethylidyne-(1-26)]-1,2-O-ethylidene-β-D-mannopyranose Acetate; 4-O-Acetyl-3,6-di-O-(3,4,6-tri-O-acetyl-β-D-mannopyranosyl-ethylidyne)-1,2-O-ethylidene-β-D-mannopyranose

Database IDs

• CAS Number: 230963-27-6
• PubChem SID: 162253383
• PubChem CID: 71312876

CALCULATED PROPERTIES

• H Acceptors: 18
• H Donor: 0
• LogD (pH = 5.5): 0.8442702
• LogD (pH = 7.4): 0.8442702
• Log P: 0.8442702
• Molar Refractivity: 189.8249 cm^3
• Polarizability: 80.31124 Å^3
• Polar Surface Area: 285.63 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A173765

An intermediate for synthesis of bioactive oligosaccharides using 1,2-O-Ethylidene-α-D-gluco- and -β-D-Mannopyranose as the acceptors and acetobromo sugars as the donors via ortho ester intermediates.

REFERENCES

• Sharp, J., et al.: J. Biol. Chem., 259, 11312 (1984)
• Cheong, J., et al.: Plant Cell, 3, 137 (1984)
• Mandal, D., et al.: Biochemistry, 33, 1157 (1984)