(-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil

Base Information

• Chemical Name: (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil
• CAS No.: 330805-78-2
• Molecular Formula: C₂₃H₃₀F₂N₂O₄Si
• Molecular Weight: 464.585

Synonyms:(-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil

Chemical Property of (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil

Chemical Property:

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Technology Process of (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil

There total 8 articles about (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N₃-benzoyl-5-fluorouracil 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: 56.0%

(+)-(1R,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol (330805-66-8) + 3-benzoyl-5-fluorouracil (61251-77-2) → (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N3-benzoyl-5-fluorouracil (330805-78-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(00)00482-1

Reference yield:

(-)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-enoic acid ethylester (279674-84-9) → (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N3-benzoyl-5-fluorouracil (330805-78-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 270 mg / lithium aluminum hydride / diethyl ether / 1.5 h / -40 - -35 °C

2: pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

3: 115 mg / tetrahydrofuran / 1.5 h / -78 °C

4: 90 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 0.5 h

5: 42 percent / H₂ / 10 percent Pd/C / cyclohexane / 2 h / 20 °C

6: 56 percent / Ph₃P; DEAD / dioxane; dimethylformamide / 3 h / 20 °C

With lithium aluminium tetrahydride; Grubbs catalyst first generation; hydrogen; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)00482-1

Reference yield:

(+)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-ol (279674-85-0) → (-)-1-[(1S,4S)-4-tert-butyldimethylsilyloxymethyl-4-fluorocyclopentan-1-yl]-N3-benzoyl-5-fluorouracil (330805-78-2)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

2: 115 mg / tetrahydrofuran / 1.5 h / -78 °C

3: 90 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 0.5 h

4: 42 percent / H₂ / 10 percent Pd/C / cyclohexane / 2 h / 20 °C

5: 56 percent / Ph₃P; DEAD / dioxane; dimethylformamide / 3 h / 20 °C

With Grubbs catalyst first generation; hydrogen; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)00482-1

upstream raw materials:

(+)-(1R,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol

3-benzoyl-5-fluorouracil

(+)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-ol

(-)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-enoic acid ethylester

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