(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

Base Information

• Chemical Name: (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
• CAS No.: 646521-58-6
• Molecular Formula: C₃₆H₅₀N₄O₆Si₂
• Molecular Weight: 690.987
• Mol file: 646521-58-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 2 articles about (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 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: 63.0%

N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten (325771-73-1) + 2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine (667411-75-8) → (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)

Guidance literature:

2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine; With N,O-bis-(trimethylsilyl)-acetamide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten; With triphenyl-arsane; N-ethyl-N,N-diisopropylamine; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1039/b502799c

Reference yield: 63.0%

N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten (325771-73-1) + N-(5-iodo-4-trimethylsilanyloxy-pyrimidin-2-yl)-benzamide → (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)

Guidance literature:

With palladium diacetate; triphenyl-arsane; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1081/NCN-120022832

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,5R)-5-(2-Benzoylamino-6-oxo-1,6-dihydro-pyrimidin-5-yl)-2-hydroxymethyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 20 ℃; for 6h;

DOI:10.1081/NCN-120022832

upstream raw materials:

N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten

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

Downstream raw materials:

(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

(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