(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol

• ChemBase ID: 162359
• Molecular Formular: C32H33N5O5
• Molecular Mass: 567.63492
• Monoisotopic Mass: 567.24816918
• SMILES: n1cnc2c(c1NC)ncn2[C@H]1C[C@@H]([C@H](O1)COC(c1ccc(cc1)OC)(c1ccc(cc1)OC)c1ccccc1)O
• Canonical SMILES: COc1ccc(cc1)C(c1ccc(cc1)OC)(c1ccccc1)OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1ncnc2NC
• InChI: InChI=1S/C32H33N5O5/c1-33-30-29-31(35-19-34-30)37(20-36-29)28-17-26(38)27(42-28)18-41-32(21-7-5-4-6-8-21,22-9-13-24(39-2)14-10-22)23-11-15-25(40-3)16-12-23/h4-16,19-20,26-28,38H,17-18H2,1-3H3,(H,33,34,35)/t26-,27+,28+/m0/s1
• InChIKey: OKZZBPBWGABLJR-UPRLRBBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol
• IUPAC Traditional name: (2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[6-(methylamino)purin-9-yl]oxolan-3-ol
• Synonyms: 5’-O-(4,4'-Dimethoxytriphenylmethyl)-N6-methyl-2'-deoxyadenosine; 5'-O-DMT-2'-deoxy-N-methyl-adenosine; 5'-O-DMT-N6-methyl-2'-deoxyadenosine; 5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-N-methyladenosine

Database IDs

• CAS Number: 98056-69-0
• PubChem SID: 162256494
• PubChem CID: 10897065

CALCULATED PROPERTIES

• Acid pKa: 13.9820795
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 4.4990687
• LogD (pH = 7.4): 4.5947466
• Log P: 4.5961175
• Molar Refractivity: 159.9061 cm^3
• Polarizability: 61.303516 Å^3
• Polar Surface Area: 112.78 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B489900

5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-N-methyladenosine is a 5’-O-(4,4'-Dimethoxytriphenylmethy) substitued derivative of the 2’-deoxy N-methyl analogue of Adenosine. It is used in the preparation of oligonucleotides containing N6-methyladenine

REFERENCES

• Ono, A. et al.: Nucleic Acids Res., 15, 219 (1987)
• Guy, A. et al.: Helv. Chim. Acta, 69, 1034 (1987)