(2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Base Information

• Chemical Name: (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 1268383-09-0
• Molecular Formula: C₃₅H₃₄N₆O₇
• Molecular Weight: 650.691
• Mol file: 1268383-09-0.mol

Synonyms:(2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property of (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

There total 10 articles about (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 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:

C29H38N6O8 (1268383-04-5) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → (2R,3S,5R)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-07-8) + (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-09-0)

Guidance literature:

C₂₉H₃₈N₆O₈; With sodium hydride; In tetrahydrofuran; oil; at 20 ℃; Inert atmosphere;

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride; In tetrahydrofuran; oil; at 20 ℃; for 1h;

With silica gel; at 90 ℃; for 15h; under high vacuum;

DOI:10.1016/j.tetlet.2010.11.122

Reference yield:

tert-butyl [4-amino-5-(benzyloxy)-1-(but-3-enyl)-1,2-dihydro-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-25-0) → (2R,3S,5R)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-07-8) + (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-09-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

3.1: sodium periodate / dichloromethane; water / 20 °C

4.1: 1,2-dichloro-ethane / 24 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; oil / 20 °C / Inert atmosphere

5.2: 1 h / 20 °C

5.3: 15 h / 90 °C / under high vacuum

With dmap; sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; oil; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2010.11.122

Reference yield:

tert-butyl [5-(benzyloxy)-1-(but-3-enyl)-4-(di-tert-butylaminodicarbonate)-1,2-dihydro-2-oxopyrimido[4,5-d]pyrimidin-7-yl]-N-(methyl)carbamate (1268383-26-1) → (2R,3S,5R)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-07-8) + (2R,3S,5S)-5-(4-amino-5-(benzyloxy)-7-(methylamino)-2-oxopyrimido[4,5-d]pyrimidin-1(2H)-yl)-2-((4-methylphenylcarbonyloxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (1268383-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 20 °C

2.1: sodium periodate / dichloromethane; water / 20 °C

3.1: 1,2-dichloro-ethane / 24 h / 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; oil / 20 °C / Inert atmosphere

4.2: 1 h / 20 °C

4.3: 15 h / 90 °C / under high vacuum

With sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; oil; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2010.11.122

upstream raw materials:

4-(but-3-enylamino)-6-chloro-2-(methylamino)pyrimidine-5-carbaldehyde

4-(benzyloxy)-6-(but-3-enylamino)-2-(methylamino)pyrimidine-5-carbaldehyde

tert-butyl [4-(benzyloxy)-6-(but-3-enylamino)-5-formylpyrimidin-2-yl]-N-(methyl)carbamate

tert-butyl [4-(benzyloxy)-6-(but-3-enylamino)-5-((hydroxyimino)methyl)pyrimidin-2-yl]-N-(methyl)carbamate