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

Base Information

• Chemical Name: N⁶-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine
• CAS No.: 233266-17-6
• Molecular Formula: C₄₈H₄₅N₅O₆
• Molecular Weight: 787.915

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

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

Chemical Property:

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

There total 13 articles about N⁶-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}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: 70.0%

(R)-methoxyphenylacetic acid (3966-32-3) + mono-4-methoxytrityl chloride (14470-28-1) + N6-Benzoyl-9-[(1S,3R,4S)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine (233266-09-6) → N6-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-17-6) + N6-Benzoyl-9-{(1R,3S,4R)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-16-5)

Guidance literature:

mono-4-methoxytrityl chloride; N⁶-Benzoyl-9-[(1S,3R,4S)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine; With pyridine; at 20 ℃; for 2h;

(R)-methoxyphenylacetic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield:

(R)-methoxyphenylacetic acid (3966-32-3) + mono-4-methoxytrityl chloride (14470-28-1) + N6-Benzoyl-9-[(1R,3S,4R)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine (233266-08-5) → N6-Benzoyl-9-{(1S,3R,4S)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-17-6) + N6-Benzoyl-9-{(1R,3S,4R)-4-(monomethoxytrityl)oxymethyl-3-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-16-5)

Guidance literature:

mono-4-methoxytrityl chloride; N⁶-Benzoyl-9-[(1R,3S,4R)-4-hydroxymethyl-3-hydroxycyclohexanyl]adenine; With pyridine; at 20 ℃; for 2h;

(R)-methoxyphenylacetic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 7h;

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-[(R)-(O-methylmandelyl)oxy]cyclohexanyl}adenine (233266-17-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 42 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: KOH / methanol / 0.5 h

3.1: AcOH; H₂O / 50 °C

4.1: pyridine / 1 h / 0 °C

5.1: pyridine / 2 h / 20 °C

6.1: NH₃; H₂O / methanol / 0.5 h

7.1: pyridine / 2 h / 20 °C

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

With pyridine; dmap; potassium hydroxide; ammonia; water; acetic acid; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1.1: Acylation / 2.1: deacylation / 3.1: detritylation / 4.1: Substitution / 5.1: Acylation / 6.1: desilylation / 7.1: Substitution / 7.2: Esterification;

upstream raw materials:

(R)-methoxyphenylacetic acid

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

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

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

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