2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one

Base Information

• Chemical Name: 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one
• CAS No.: 667411-76-9
• Molecular Formula: C₂₈H₄₃N₃O₅Si₂
• Molecular Weight: 557.838
• Mol file: 667411-76-9.mol

Synonyms:2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one

Chemical Property of 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one

There total 1 articles about 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one 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: 68.0%

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose (173327-56-5) + 2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine (667411-75-8) → 2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one (667411-76-9)

Guidance literature:

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

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose; With palladium diacetate; triphenyl-arsane; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1081/NCN-120025239

Reference yield:

2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one (667411-76-9) → N-[5-((2R,5R)-4-Hydroxy-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-benzamide

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 28h;

DOI:10.1081/NCN-120025239

Reference yield:

2-benzoylamino-5-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pent-2-enofuranosyl]-3H-pyrimidin-4-one (667411-76-9) → N4-benzoyl-2'-deoxypseudoisocytidine (667411-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HF*pyridine / tetrahydrofuran / 28 h / 20 °C

2: 289 mg / AcOH; NaBH(OAc)3 / acetonitrile / 2 h / -15 - 20 °C

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

DOI:10.1081/NCN-120025239

upstream raw materials:

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose

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

Downstream raw materials:

N⁴-benzoyl-2'-deoxypseudoisocytidine

N-(5-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-1,6-dihydro-pyrimidin-2-yl)-benzamide