N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine

Base Information

• Chemical Name: N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine
• CAS No.: 233266-15-4
• Molecular Formula: C₃₉H₃₇N₅O₄
• Molecular Weight: 639.754

Synonyms:N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine

Chemical Property of N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine

There total 17 articles about N⁶-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine 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%

N6-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-17-6) → N6-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine (233266-15-4)

Guidance literature:

With potassium hydroxide; In methanol;

Reference yield:

(1S,2R,5R)-5-(6-{[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-2-trityloxymethyl-cyclohexanol → N6-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine (233266-15-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 42 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

2: KOH / methanol / 0.5 h

3: AcOH; H₂O / 50 °C

4: pyridine / 1 h / 0 °C

5: pyridine / 2 h / 20 °C

6: NH₃; H₂O / methanol / 0.5 h

7: pyridine / 2 h / 20 °C

With pyridine; dmap; potassium hydroxide; ammonia; water; acetic acid; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1: Acylation / 2: deacylation / 3: detritylation / 4: Substitution / 5: Acylation / 6: desilylation / 7: Substitution;

Reference yield:

mono-4-methoxytrityl chloride (14470-28-1) → N6-Benzoyl-9-[(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-hydroxycyclohexanyl]adenine (233266-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 2 h / 20 °C

1.2: DCC; DMAP / CH₂Cl₂ / 7 h / 0 - 20 °C

2.1: 94 percent / KOH / methanol

With pyridine; potassium hydroxide; In methanol; 1.1: Substitution / 1.2: Esterification / 2.1: Substitution;

upstream raw materials:

mono-4-methoxytrityl chloride

N⁶-Benzoyl-9-[(1R,3S,4R)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine

N⁶-Benzoyl-9-[(1S,3R,4S)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine

N⁶-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine

Downstream raw materials:

Diisopropyl-phosphoramidous acid (1R,2S,5S)-5-(6-benzoylamino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-cyclohexyl ester 2-cyano-ethyl ester

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