110582-31-5

Basic information

• Product Name: <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
• Synonyms: <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
• CAS NO: 110582-31-5
• Molecular Weight: 524.49
• Mol File: 110582-31-5.mol

Chemical Properties

• CAS DataBase Reference: <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(CAS DataBase Reference)
• NIST Chemistry Reference: <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(110582-31-5)
• EPA Substance Registry System: <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(110582-31-5)

Safety Data

• Hazardous Substances Data: 110582-31-5(Hazardous Substances Data)

Upstream product

• 79-37-8 oxalyl dichloride 
• 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 
• 96881-37-7 1-benzyl-7-formylwye 
• 96854-31-8 -4-<1-Benzyl-4,9-dihydro-4,6-dimethyl-9-oxo-1H-imidazo<1,2-a>purin-7-yl>-2-<(methoxycarbonyl)amino>-3-butenoic Acid Methyl Ester 

Downstream Products

• 35693-91-5 wybutine 
• 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 
• 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 
• 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 

Relevant articles and documents

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 β-hydroxywybutines, the most probable alternatives for the hypermodified base of rat liver phenylalanine transfer ribonucleic acid

Deoxygenation of the 1,2-glycol (±)-5 was achieved at the position adjacent to the heterocycle through the cyclic carbonate (±)-14, providing the monohydroxy compound 6. This new method of regioselective deoxygenation was employed for the first synthesis

Formation of cyclic carbonates in the reactions of 1,2-glycols with oxalyl chloride

Oxalyl chloride reacts with a wide range of 1,2-glycols in the presence of triethylamine to produce 1,3-dioxolan-2-ones together with 1,4-dioxane-2,3-diones; the ratio of the products largely depends on the structure of the 1,2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.

Cyclocondensation of oxalyl chloride with 1,2-glycols

Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-l, and erythro-1,2-disubstituted ethylene glycols 1f, m, o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n, p, q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate of the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.

SYNTHESIS OF OPTICALLY ACTIVE FORMS OF HYDROXY-Y BASE, THE MINOR COMPONENT OF RAT LIVER PHENYLALANINE TRANSFER RIBONUCLEIC ACID

-β-Hydroxywybutine (6) and its -isomer (9) have been synthesized as the most probable alternatives for hydroxy-Y base isolated from rat liver phenylalanine tRNA.