2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE

Base Information

• Chemical Name: 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE
• CAS No.: 869354-99-4
• Molecular Formula: C₁₄H₂₁N₇O₄
• Molecular Weight: 351.365
• Mol file: 869354-99-4.mol

Synonyms:2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE

Chemical Property of 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE

Chemical Property:

• PSA: 133.38000
• LogP: -0.91640

Purity/Quality:

≥ 95% ^*data from raw suppliers

2-(Dimethylaminomethylidene)amino-6-methoxylamino-9-(β-D-2-deoxyribofuranosyl)purine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-(Dimethylaminomethylidene)amino-6-methoxylamino-9-(β-D-2-deoxyribofuranosyl)purine is a derivative of 6-(Methylamino)purine (M287005), which is a reagent for substitution of adenine nucelotide analogs containing bicyclohexane ring system locked in northern conformation enhanced potency as receptor antagonists. Adenine methylation as an epigenic mark has been observed in single-celled organisms and also rarely in mammalian cells.

Technology Process of 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE

There total 5 articles about 2-(DIMETHYLAMINOMETHYLIDENE)AMINO-6-METHOXYLAMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE 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:

2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine (35095-93-3) → N'-{9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine (869354-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / ethanol / 4 h / 90 °C

2: NH₃ / methanol / 55 °C / overnight

3: dimethylformamide / 2 h / 50 °C

With ammonia; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84156-M

Reference yield:

2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-6-methoxyaminopurine (136986-34-0) → N'-{9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine (869354-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃ / methanol / 55 °C / overnight

2: dimethylformamide / 2 h / 50 °C

With ammonia; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84156-M

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → N'-{9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine (869354-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) KOH, tris<2-(2-methoxyethoxy)ethyl>amine / 1) MeCN, r.t., 10 min, 2) 40 min

2: 49 percent / ethanol / 4 h / 90 °C

3: NH₃ / methanol / 55 °C / overnight

4: dimethylformamide / 2 h / 50 °C

With potassium hydroxide; Tris(3,6-dioxaheptyl)amine; ammonia; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84156-M

upstream raw materials:

2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one O-methyl-oxime

N,N-dimethyl-formamide dimethyl acetal

2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine

2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-6-methoxyaminopurine

Downstream raw materials:

9-<2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl>-2-dimethyleneamino-6-methoxyaminopurine 3'-(2-cyanoethyl N,N-di-isopropylphosphoramidite)

N'-{9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine

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