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

Base Information

• Chemical Name: (2R,4S,5R)-N-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine
• CAS No.: 855519-63-0
• Molecular Formula: C₂₄H₂₄N₄O₆
• Molecular Weight: 464.478
• Mol file: 855519-63-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(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-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-hydroxy-5-hydroxymethyl pyrrolidine (855519-63-0)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at -15 - 0 ℃; for 5h;

DOI:10.1039/b502799c

Reference yield:

2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine (667411-75-8) → (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)

Guidance literature:

Multi-step reaction with 3 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

With N,O-bis-(trimethylsilyl)-acetamide; sodium tris(acetoxy)borohydride; pyridine hydrogenfluoride; acetic acid; In N,N-dimethyl-formamide; acetonitrile; 1.2: Heck reaction;

DOI:10.1039/b502799c

Reference yield:

(2R,5R)-N-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-[(tert-butyl)dimethylsilyl]oxy-5-[(tert-butyl)dimethylsilyl]oxymethyl-aza-cyclopent-3-ene (646521-58-6) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 322 mg / NaBH(OAc)3; AcOH / acetonitrile / 5 h / -15 - 0 °C

With sodium tris(acetoxy)borohydride; pyridine hydrogenfluoride; acetic acid; In acetonitrile;

DOI:10.1039/b502799c

upstream raw materials:

2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine

(2R,5R)-N-(benzyloxy)carbonyl-2-[2-(N-benzoylamino)-4-oxo-3,4-dihydropyrimidin-5-yl]-4-[(tert-butyl)dimethylsilyl]oxy-5-[(tert-butyl)dimethylsilyl]oxymethyl-aza-cyclopent-3-ene

Downstream 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

(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