1-Pyrrolidinecarboxylic acid, 5-[2-(benzoylamino)-1,4-dihydro-4-oxo-5-pyrimidinyl]-2-[[bis(4-methoxy phenyl)phenylmethoxy]methyl]-3-hydroxy-, 9H-fluoren-9-ylmethyl ester, (2R,3S,5R)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 5-[2-(benzoylamino)-1,4-dihydro-4-oxo-5-pyrimidinyl]-2-[[bis(4-methoxy phenyl)phenylmethoxy]methyl]-3-hydroxy-, 9H-fluoren-9-ylmethyl ester, (2R,3S,5R)-
• CAS No.: 646521-64-4
• Molecular Formula: C₅₂H₄₆N₄O₈
• Molecular Weight: 854.959
• Mol file: 646521-64-4.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 5-[2-(benzoylamino)-1,4-dihydro-4-oxo-5-pyrimidinyl]-2-[[bis(4-methoxy phenyl)phenylmethoxy]methyl]-3-hydroxy-, 9H-fluoren-9-ylmethyl ester, (2R,3S,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 5-[2-(benzoylamino)-1,4-dihydro-4-oxo-5-pyrimidinyl]-2-[[bis(4-methoxy phenyl)phenylmethoxy]methyl]-3-hydroxy-, 9H-fluoren-9-ylmethyl ester, (2R,3S,5R)-

There total 6 articles about 1-Pyrrolidinecarboxylic acid, 5-[2-(benzoylamino)-1,4-dihydro-4-oxo-5-pyrimidinyl]-2-[[bis(4-methoxy phenyl)phenylmethoxy]methyl]-3-hydroxy-, 9H-fluoren-9-ylmethyl ester, (2R,3S,5R)- 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-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine (667411-75-8) → (2R,4S,5R)-N-[(9-fluorenylmethoxy)carbonyl]-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-5-[(4,4'-dimethoxy)triphenylmethyl]-oxymethyl-4-hydroxy pyrrolidine (646521-64-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N,O-bis(trimethylsilyl)acetamide / dimethylformamide / 1 h / 20 °C

1.2: 63 percent / i-Pr₂NEt; AsPh₃ / Pd(OAc)2 / dimethylformamide / 22 h / 80 °C

2.1: HF-pyridine / acetonitrile / 6 h / 20 °C

3.1: 322 mg / NaBH(OAc)3; AcOH / acetonitrile / 5 h / -15 - 0 °C

4.1: 99 percent / H₂ / Pd/C / methanol / 7 h / 20 °C

5.1: aq. NaHCO₃ / tetrahydrofuran; dioxane / 4 h / 20 °C

6.1: 265 mg / pyridine / 2 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetonitrile; 1.2: Heck reaction;

DOI:10.1039/b502799c

Reference yield:

(2R,4S,5R)-N-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine (855519-63-0) → (2R,4S,5R)-N-[(9-fluorenylmethoxy)carbonyl]-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-5-[(4,4'-dimethoxy)triphenylmethyl]-oxymethyl-4-hydroxy pyrrolidine (646521-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / methanol / 7 h / 20 °C

2: aq. NaHCO₃ / tetrahydrofuran; dioxane / 4 h / 20 °C

3: 265 mg / pyridine / 2 h / 20 °C

With pyridine; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1039/b502799c

Reference yield:

(2R,5R)-5-(2-Benzoylamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-2-hydroxymethyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester → (2R,4S,5R)-N-[(9-fluorenylmethoxy)carbonyl]-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-5-[(4,4'-dimethoxy)triphenylmethyl]-oxymethyl-4-hydroxy pyrrolidine (646521-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 322 mg / NaBH(OAc)3; AcOH / acetonitrile / 5 h / -15 - 0 °C

2: 99 percent / H₂ / Pd/C / methanol / 7 h / 20 °C

3: aq. NaHCO₃ / tetrahydrofuran; dioxane / 4 h / 20 °C

4: 265 mg / pyridine / 2 h / 20 °C

With pyridine; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile;

DOI:10.1039/b502799c

upstream raw materials:

(2R,4S,5R)-N-[(9-fluorenylmethoxy)carbonyl]-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine

4,4'-dimethoxytrityl chloride

(2R,4S,5R)-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine

(2R,4S,5R)-N-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine