96854-31-8

Upstream product

• 96881-37-7 1-benzyl-7-formylwye 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 65120-81-2 1-benzyl-4,6-dimethyl-1,4-dihydro-imidazo[1,2-a]purin-9-one 
• 119484-05-8 1-benzyl-7-iodo-4,6-dimethyl-4,9-dihydro-1H-imidazo<1,2-a>purin-9-one 
• 136978-28-4 (S)-(E)-(1-benzyl-4,6-dimethyl-9-oxo-4,9-dihydro-1H-imidazo<1,2-a>purin-7-yl)-2-<(methoxycarbonyl)amino>but-3-enoic acid 
• 160351-20-2 (S)-2-<(methoxycarbonyl)amino>but-3-enoic acid 
• 148469-28-7 (R)-<2-Carboxy-2-<(methoxycarbonyl)amino>ethyl>triphenylphosphonium Chloride 

Downstream Products

• 110582-29-1 *,S^*)>-4,9-dihydro-β-hydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 110582-32-6 *,R^*)>-4,9-dihydro-β-hydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 214117-24-5 (+/-)-1-benzyl-α-<(methoxycarbonyl)amino>-β-oxo-4,6-dimethyl-9-oxo-4,9-dihydro-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 70363-52-9 (R*,S*)-β-hydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-4,9-dihydro-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 70363-52-9 (R*,R*)-β-hydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-4,9-dihydro-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 110658-45-2 <4R-<4α(S^*),5β>>-5-<1-benzyl-4,9-dihydro-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purin-7-yl>-α-<(methoxycarbonyl)amino>-2-oxo-1,3-dioxolane-4-acetic acid methyl ester 
• 110582-31-5 <4S-<4α(R^*),5β>>-5-<1-benzyl-4,9-dihydro-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purin-7-yl>-α-<(methoxycarbonyl)amino>-2-oxo-1,3-dioxolane-4-acetic acid methyl ester 
• 110582-30-4 <αS-(αR^*,βR^*,γR^*)>-1-benzyl-4,9-dihydro-β,γ-dihydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-1H-imidazol<1,2-a>purine-7-butanoic acid methyl ester 
• 110658-44-1 αS-(αR^*,βS^*,γS^*)-1benzyl-4,9-dihydro-β,γ-dihydroxy-α-<(methoxycarbonyl)amino>-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purine-7-butanoic acid methyl ester 
• 35693-91-5 wybutine 
• 65120-77-6 4-(1-benzyl-4,6-dimethyl-9-oxo-4,9-dihydro-1H-imidazo[1,2-a]purin-7-yl)-2-methoxycarbonylamino-butyric acid methyl ester 

Relevant academic research and scientific papers

Studies towards the synthesis of the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid: Improved synthesis of the base β-hydroxywybutine

An improved synthesis of the key intermediates (3 and 8) for the synthesis of β-hydroxywybutines [[R(R*,S*)]- and [S-(R*,R*)]-4], the most probable structures for the minor base from rat liver tRNA(Phc), has been achieved by the Wittig reaction between 1-benzyl-7-formylwye (1) and the phosphorane derived from (R)-2[(methoxycarbonyl)amino]-3- (triphenylphosphonio)propanoate (10), followed by methylation, OsO4 oxidation, and cyclocondensation with COCI2 in the presence of pyridine. The racemic forms of β-hydroxywybutines [(R*,S*)- and (R*,R*)-4], which were required for the determination of the optical purity of [R-(R*,S*)]- and [S-(R*,R*)]-4 by means of chiral HPLC, were conveniently prepared through pyrolysis of the cyclic carbonate 3 followed by NaBH4 reduction and catalytic hydrogenolysis. The samples of [R-(R*,S*)]- and [S-(R*,R*)]-4 were thus shown to be optically pure.

Synthesis of 3-β-D-Ribofuranosylwybutine, the Most Probable Structure for the Hypermodified Nucleoside Isolated from Yeast Phenylalanine Transfer Ribonucleic Acids

An alternative synthesis of the key intermediate 8 for the synthesis of wybutine 1 has been attained through the Heck reaction between (S)-N-(methoxycarbonyl)vinylglycine 13 and 1-benzyl-7-iodowye 7.The nucleoside version of this method using 7-iodo-3-(2,

Synthesis and absolute configuration of wybutine, the fluorescent minor base from phenylalanine transfer ribonucleic acids

The phosphonium chloride 6 having an optically active amino acid moiety was synthesized from (S)-serine benzyl ester tosylate (2b) through a six-step route. The utility of 6 as a reagent for the Wittig reaction was exemplified in the olefination with benz

ACCESS TO THE SYNTHESIS OF WYBUTOSINE, THE FIRST TRICYCLIC FLUORESCENT NUCLEOSIDE ISOLATED FROM PHENYLALANINE TRANSFER RIBONUCLEIC ACIDS

An improved synthesis of the key intermediate 5 for the chiral syntheses of wybutine (1c) and hydroxywybutine (1d) has been achieved by palladium-catalyzed vinylation, which has been utilized for the first synthesis of 3-β-D-ribofuranosylwybutine (2c).

SYNTHESIS OF (S)-(-)-WYBUTINE, THE FLUORESCENT MINOR BASE FROM YEAST PHENYLALANINE TRANSFER RIBONUCLEIC ACIDS

The Wittig reaction of 1-benzyl-7-formylwye (12) with (R)-ethyl>triphenylphosphonium chlorid (8) followed by successive methylation and reduction gave (-)-wybutine .