*,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

Base Information

• Chemical Name: *,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
• CAS No.: 110582-29-1
• Molecular Formula: C₁₆H₂₀N₆O₆
• Molecular Weight: 392.371
• Mol file: 110582-29-1.mol

Synonyms:

Chemical Property of *,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of *,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

There total 13 articles about *,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 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: 45.0%

<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) → wybutine (35693-91-5) + *,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 (110582-29-1,70363-52-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 60 ℃; for 16h; under 3800 Torr;

DOI:10.1016/0040-4020(95)00302-O

Reference yield: 19.0%

<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 (110582-30-4) → *,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 (110582-29-1,70363-52-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 60 ℃; for 22h; under 4560 Torr;

DOI:10.1016/0040-4020(95)00302-O

Reference yield:

[S-(E)]-4-[4,6-dimethyl-9-oxo-3-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-4,9-dihydro-3H-imidazo[1,2-a]purin-7-yl]-2-[(methoxycarbonyl)amino]-3-butenoic acid methyl ester (189103-74-0) → *,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 (110582-29-1,70363-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 50 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / 2-methyl-propan-2-ol; acetone; aq. phosphate buffer / 4 h / 20 °C / pH 6

2: 80 percent / pyridine / CH₂Cl₂; benzene / 0.25 h / 0 °C

3: 29 percent / H₂ / Pd/C / methanol / 3 h / 40 °C / 760 Torr

4: 5 mg / 0.1 N aq. HCl / 1 h / 20 °C

With pyridine; hydrogenchloride; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.50.1318

upstream raw materials:

<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

<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

(αS,βR)-β-hydroxy-α-[(methoxycarbonyl)amino]-4,6-dimethyl-9-oxo-3-β-D-ribofuranosyl-4,9-dihydro-3H-imidazo[1,2-a]purine-7-butanoic acid methyl ester

(αS,βR)-β-hydroxy-α-[(methoxycarbonyl)amino]-4,6-dimethyl-9-oxo-3-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-4,9-dihydro-3H-imidazo[1,2-a]purine-7-butanoic acid methyl ester