[(2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-3-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-[(acetyloxy)methyl]-5-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-methyl-5-{[(1S,4S,5S,6S)-4,5,6-tris(acetyloxy)-3-[(acetyloxy)methyl]cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}oxan-2-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 158828
• Molecular Formular: C51H69NO31
• Molecular Mass: 1192.08166
• Monoisotopic Mass: 1191.38535443
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)N[C@@H]1[C@H]([C@H]([C@H](C(=C1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C)COC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@H](O[C@@H]2[C@H](COC(=O)C)O[C@H]([C@H]([C@H]2OC(=O)C)OC(=O)C)OC(=O)C)[C@H]([C@H]([C@@H]1O[C@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)N[C@H]1C=C(COC(=O)C)[C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C51H69NO31/c1-19-37(52-34-15-33(16-66-20(2)53)38(70-23(5)56)43(73-26(8)59)39(34)71-24(6)57)42(72-25(7)58)46(76-29(11)62)49(69-19)82-40-36(18-68-22(4)55)81-51(48(78-31(13)64)45(40)75-28(10)61)83-41-35(17-67-21(3)54)80-50(79-32(14)65)47(77-30(12)63)44(41)74-27(9)60/h15,19,34-52H,16-18H2,1-14H3/t19-,34+,35-,36-,37-,38+,39+,40-,41-,42+,43+,44+,45+,46-,47-,48-,49-,50-,51-/m1/s1
• InChIKey: DEPYMLFJKYFQBH-HJCIOCNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-3-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-[(acetyloxy)methyl]-5-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-methyl-5-{[(1S,4S,5S,6S)-4,5,6-tris(acetyloxy)-3-[(acetyloxy)methyl]cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}oxan-2-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6S)-4,5,6-tris(acetyloxy)-3-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-[(acetyloxy)methyl]-5-{[(2R,3R,4S,5R,6R)-3,4-bis(acetyloxy)-6-methyl-5-{[(1S,4S,5S,6S)-4,5,6-tris(acetyloxy)-3-[(acetyloxy)methyl]cyclohex-2-en-1-yl]amino}oxan-2-yl]oxy}oxan-2-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: O-2,3-Di-O-acetyl-4,6-dideoxy-4-[[4,5,6-tris(acetyloxy)-3-[(acetyloxy)methyl]-2-cyclohexen-1-yl]amino]-α-D-glucopyranosyl-(1-4)-O-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1-4)-α-D-glucopyranose 1,2,3,6-Tetraacetate; Acarbose Tridecaacetate

Database IDs

• CAS Number: 117065-98-2
• PubChem SID: 162252963
• PubChem CID: 71312705

CALCULATED PROPERTIES

• H Acceptors: 19
• H Donor: 1
• LogD (pH = 5.5): -3.718524
• LogD (pH = 7.4): -2.15634
• Log P: -1.8799285
• Molar Refractivity: 256.5719 cm^3
• Polarizability: 107.521255 Å^3
• Polar Surface Area: 400.08 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - A123505

An intermediate in the preparation of Acarbose.

REFERENCES

• Shibata, Y., et al.: Carbohydrate Res., 189, 309 (1989)