(2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol

Base Information

• Chemical Name: (2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol
• CAS No.: 98056-69-0
• Molecular Formula: C32H33 N5 O5
• Molecular Weight: 567.645
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID90447501
• Wikidata: Q82266382
• Mol file: 98056-69-0.mol

Synonyms:98056-69-0;5'-O-DMT-N6-methyl-2'-deoxyadenosine;(2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol;5'-O-DMT-N6-Me-2'-dA;5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-N-methyladenosine;2'-Deoxy-5'-O-DMT-N6-methyladenosine;(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[6-(methylamino)purin-9-yl]oxolan-3-ol;5'-O-(DIMETHOXYTRITYL)-N6-METHYL-2'-DEOXYADENOSINE;MFCD00079127;2-Chloroethyln-butylether;DTXSID90447501;HG1043;AC-32203;BS-29853;PD167011;5/'-O-DMT-N6-methyl-2/'-deoxyadenosine;HY-138604;CS-0159290;A858589;J-700131;(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol

Chemical Property of (2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol

Chemical Property:

• PSA: 112.78000
• LogP: 4.61530
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 567.24816917
• Heavy Atom Count: 42
• Complexity: 808

Purity/Quality:

98%, ^*data from raw suppliers

5''-O-[Bis(4-methoxyphenyl)phenylmethyl]-2''-deoxy-N-methyladenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C2C(=NC=N1)N(C=N2)C3CC(C(O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O
• Isomeric SMILES: CNC1=C2C(=NC=N1)N(C=N2)[C@H]3C[C@@H]([C@H](O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O
• Uses: 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 residues in the GATC site.

Technology Process of (2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol

There total 2 articles about (2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-(methylamino)-9H-purin-9-yl)tetrahydrofuran-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-6-methyl-2'-deoxyribofuranosil adenine (2002-35-9) → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N6-methyladenosine (98056-69-0)

Guidance literature:

With pyridine; at 20 ℃; for 6h;

DOI:10.1039/c8ob03112f

Reference yield:

N-1-methyl-2'-deoxyribofuranosiladenine iodide (74873-17-9) → 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N6-methyladenosine (98056-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / NaOH / 90 °C

2: 55 percent / pyridin / 1 h / Ambient temperature

With pyridine; sodium hydroxide;

DOI:10.1002/hlca.19860690511

Reference yield: 100.0%

bis(N,N-diisopropylamino)methoxyphosphine (92611-10-4) + 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N6-methyladenosine (98056-69-0) → Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester (106023-62-5)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane;

upstream raw materials:

4,4'-dimethoxytrityl chloride

N-6-methyl-2'-deoxyribofuranosil adenine

N-1-methyl-2'-deoxyribofuranosiladenine iodide

Downstream raw materials:

<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine-3'-O-yl>(methoxy)morpholinophosphine

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester

Phosphoric acid dibenzyl ester (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

Phosphoric acid dibenzyl ester (2R,3S,5R)-2-hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester