62853-19-4

Basic information

• Product Name: Benzamide, N-[1-(2,3-dihydroxypropyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-, (S)-
• CAS NO: 62853-19-4
• Molecular Formula: C14H15N3O4
• Molecular Weight: 289.291
• Mol File: 62853-19-4.mol

Chemical Properties

• CAS DataBase Reference: Benzamide, N-[1-(2,3-dihydroxypropyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[1-(2,3-dihydroxypropyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-, (S)-(62853-19-4)
• EPA Substance Registry System: Benzamide, N-[1-(2,3-dihydroxypropyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-, (S)-(62853-19-4)

Safety Data

• Hazardous Substances Data: 62853-19-4(Hazardous Substances Data)

Upstream product

• 127757-42-0 N-[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 75-77-4 chloro-trimethyl-silane 
• 98-88-4 benzoyl chloride 
• 55559-70-1 1-(S)-(2,3-dihydroxypropyl)cytosine 
• 127757-35-1 1-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methoxy-1H-pyrimidin-2-one 
• 127757-41-9 N-[3-Benzoyl-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-2-oxo-2,3-dihydro-1H-pyrimidin-(4E)-ylidene]-benzamide 
• 648881-65-6 N-(1-allyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 26661-13-2 4-N-benzoylcytosine 
• 58274-10-5 4-amino-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrimidin-2-one 

Downstream Products

• 132336-34-6 (S)-N₁-[2-hydroxy-3-(triphenylmethoxy)propyl]-N₄-benzoylcytosine 
• 132336-36-8 diethyl (S)-4-N-benzoyl-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine 
• 132336-37-9 N⁴-benzoyl-1-(S)-(3-hydroxy-2-phosphonomethoxypropyl)cytosine 
• 113852-37-2 cidofovir 
• 120362-37-0 disodium salt of 1-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine 
• 127785-75-5 Benzoic acid (S)-1-(4-benzoylamino-2-oxo-2H-pyrimidin-1-ylmethyl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl ester 
• 127757-40-8 (S)-1-(3-(4,4′-dimethoxytrityloxy)-2-hydroxypropyl)-N4-benzoylcytosine 

Relevant articles and documents

Method for synthesizing antiviral drugs cidofovir and buciclovir

The invention relates to a method for synthesizing antiviral drugs, i.e., cidofovir and buciclovir, belonging to the field of asymmetric synthesis in organic chemistry. According to the invention, pyrimidine with position 1 substituted by an allyl group or purine with position 9 substituted by a butenyl group are used as raw materials and subjected to asymmetric dihydroxylation so as to obtain a key chiral intermediate of cidofovir or buciclovir, and then a multi-step reaction is carried out so as to obtain cidofovir or buciclovir. With such a route in the invention, the reaction raw materialsare easily available, stereoselectivity is high, and the chiral dihydroxynucleoside intermediates are obtained after the reaction, and the cidofovir and buciclovir can be smoothly obtained after multiple steps of transformation.

Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir

An efficient method to construct chiral acyclic nucleosides via Sharpless asymmetric dihydroxylation of N-allylpyrimidines or N-alkenylpurines is reported. A range of chiral acyclic nucleosides with two adjacent hydroxyl groups present on the side chains could be produced in good yields (up to 97% yield) and excellent enantioselectivities (90-99% ee). The synthetic utility of the reaction was demonstrated by the catalytic asymmetric synthesis of (S)-Cidofovir and (R)-Buciclovir.

SYNTHESIS OF (3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL) DERIVATIVES OF HETEROCYCLIC BASES

Analogs of antiviral 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA, I), containing modofied heterocyclic base, were prepared from racemic or (S)-N-(2,3-dihydroxypropyl) derivatives II.Compounds II are heated with chloromethylphosphonyl dichlor