135697-25-5

Basic information

• Product Name: Benzamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-4-(1,1-dimethylethyl)-
• CAS NO: 135697-25-5
• Molecular Formula: C15H17N3O2
• Molecular Weight: 271.319
• Mol File: 135697-25-5.mol

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-4-(1,1-dimethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-4-(1,1-dimethylethyl)-(135697-25-5)
• EPA Substance Registry System: Benzamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-4-(1,1-dimethylethyl)-(135697-25-5)

Safety Data

• Hazardous Substances Data: 135697-25-5(Hazardous Substances Data)

Upstream product

• 71-30-7 Cytosine 
• 1710-98-1 p-tert-butyl benzoyl chloride 

Downstream Products

• 1026181-90-7 4-tert-butyl-N-(2-trimethylsilanyloxy-pyrimidin-4-yl)-benzamide 
• 1235489-06-1 C₂₃H₃₀N₄O₆ 
• 135697-51-7 C₆₅H₈₂N₁₂O₁₂ 
• 135697-45-9 4-tert-Butyl-benzoic acid 2-({(S)-5-{(S)-5-tert-butoxycarbonylamino-6-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-hexanoylamino}-6-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-hexanoyl}-methyl-amino)-ethyl ester 
• 135697-46-0 4-tert-Butyl-benzoic acid 2-({(S)-4-{(S)-4-tert-butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoylamino}-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoyl}-methyl-amino)-ethyl ester 
• 135697-41-5 {(S)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-4-[(S)-1-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-4-(piperidin-1-ylcarbamoyl)-butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester 
• 135697-42-6 {(S)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-[(S)-1-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-3-(piperidin-1-ylcarbamoyl)-propylcarbamoyl]-propyl}-carbamic acid tert-butyl ester 
• 135697-38-0 (S)-2-<<5-<<(1,1-dimethylethoxy)carbonyl>amino>-6-<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>-1-oxohexyl>methylamino>ethyl 4-(1,2-dimethylethyl)benzoate 
• 135697-40-4 (S)-2-<<4-<<(1,1-dimethylethoxy)carbonyl>amino>-5-<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>-1-oxopentyl>methylamino>ethyl 4-(1,2-dimethylethyl)benzoate 
• 135697-32-4 (S)-5-tert-Butoxycarbonylamino-6-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-hexanoic acid 4-nitro-phenyl ester 
• 135697-33-5 (S)-4-tert-Butoxycarbonylamino-5-[4-(4-tert-butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-pentanoic acid 4-nitro-phenyl ester 
• 135697-35-7 (S)-1,2-dimethyl <1-<<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-5-oxo-5-(1-piperidinylamino)pentyl>carbamate 
• 135697-36-8 (S)-1,1-dimethylethyl <1-<<4-<<4-(1,1-dimethylethyl)benzoyl>amino>-1,2-dihydro-2-oxo-1-pyrimidinyl>methyl>-4-oxo-4-(1-piperidinylamino)butyl>carbamate 
• 135697-37-9 {(S)-1-[4-(4-tert-Butyl-benzoylamino)-2-oxo-2H-pyrimidin-1-ylmethyl]-4-[(2-hydroxy-ethyl)-methyl-carbamoyl]-butyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy

The preparation of novel monomethoxytrityl (Mmt) protected monomers for the synthesis of polyamide nucleic acids (PNAs) is described. The use of base-labile acyl-type nucleobase protecting groups and of a succinyl-linked solid-support offers a synthetic strategy to standard oligonucleotide synthesis conditions. This strategy has been successfully applied for the synthesis of PNAs of mixed base sequence.

Nucleic acid derivatives

A compound which comprises a backbone having a plurality of chiral carbon atoms, the backbone bearing a plurality of ligands each being individually bound to a chiral carbon atom of the plurality of chiral carbon atoms, the ligands including one or more pair(s) of adjacent ligands each containing a moiety selected from the group consisting of a naturally occurring nucleobase and a nucleobase binding group, wherein moieties of the one or more pair(s) are directly linked to one another via a linker chain; building blocks for synthesizing the compound; and rises of the compound, particularly in antisense therapy.

Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N, N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N9/N7-substituted guanines based on their 13C NMR chemical-shift differences. The Royal Society of Chemistry 2000.

Substituted N-ethylglycine derivatives for preparing PNA and PNA/DNA hybrids

There are described N-ethylglycine derivatives of the formula I in which PG is a urethane-type or trityl-type amino protective group which is labile to weak acids, X is NH, O or S, Y is CH2, NH or O, and B' are bases customary in nucleotide chemistry, the exocyclic amino or hydroxyl groups of which being protected by suitable, known protective groups, or are base substitute compounds, and their salts with tert-organic bases, as well as a process for their preparation. The N-ethylglycine derivatives of the formula I are used in the preparation of PNA and PNA/DNA hybrids.

Acyclic Nucleic Acid Analogues: Synthesis and Oligomerization of γ,4-Diamino-2-oxo-1(2H)-pyrimidinepentanoic Acid and δ,4-Diamino-2-oxo-1(2H)-pyrimidinehexanoic Acid

Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base exocyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form.Oligomerization was achieved by activation of the carboxylic group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethlformamide or dimethyl sulfoxide.A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers.The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.