(2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate

Base Information

• Chemical Name: (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate
• CAS No.: 1439900-80-7
• Molecular Formula: C₂₇H₃₉N₄O₁₁P
• Molecular Weight: 626.601
• Mol file: 1439900-80-7.mol

Synonyms:(2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate

Chemical Property of (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate

There total 14 articles about (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate 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:

tert-butyl ((2R,3R,4S,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)carbamate (1439900-78-3) + N-[P-pentafluorophenyl-P-phenyl]-L-alanine isopropyl ester (1520010-86-9) → (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate (1439900-79-4) + (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate (1439900-80-7)

Guidance literature:

With 1-methyl-1H-imidazole; In dichloromethane; at -10 - 20 ℃; Overall yield = 53 %; Overall yield = 299 mg;

Reference yield:

methyl α-D-ribofuranoside (52485-92-4) → (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate (1439900-80-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C

1.2: 16 h / 0 - 20 °C

2.1: tin(IV) chloride / dichloromethane / 24 h / 0 °C

3.1: Dess-Martin periodane / dichloromethane / 24 h / 0 - 20 °C

4.1: titanium(IV) tetraethanolate / tetrahydrofuran / 6 h / 20 - 60 °C

5.1: tetrahydrofuran / 0.5 h / -78 °C

6.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C

7.1: pyridine / dichloromethane / 3 h / -40 - 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 85 °C

8.2: 21 h / 0 - 80 °C

9.1: sodium hydroxide; sodium carbonate; water / methanol / 48 h / 80 °C

10.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 6 h / 20 °C

11.1: triethylamine / acetonitrile; water

12.1: 1-methyl-1H-imidazole / dichloromethane / -10 - 20 °C

With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; titanium(IV) tetraethanolate; N,O-bis-(trimethylsilyl)-acetamide; 10 wt% Pd(OH)2 on carbon; water; hydrogen; tin(IV) chloride; sodium hydride; sodium carbonate; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (2S)-isopropyl 2-(((2R,3S,4R,5R)-4-((tert-butoxycarbonyl)amino)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-O-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy)(phenoxy)-phosohoryl)amino)propanoate (1439900-80-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sulfuric acid / methanol / 24 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C

2.2: 16 h / 0 - 20 °C

3.1: tin(IV) chloride / dichloromethane / 24 h / 0 °C

4.1: Dess-Martin periodane / dichloromethane / 24 h / 0 - 20 °C

5.1: titanium(IV) tetraethanolate / tetrahydrofuran / 6 h / 20 - 60 °C

6.1: tetrahydrofuran / 0.5 h / -78 °C

7.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C

8.1: pyridine / dichloromethane / 3 h / -40 - 20 °C

9.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 85 °C

9.2: 21 h / 0 - 80 °C

10.1: sodium hydroxide; sodium carbonate; water / methanol / 48 h / 80 °C

11.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 6 h / 20 °C

12.1: triethylamine / acetonitrile; water

13.1: 1-methyl-1H-imidazole / dichloromethane / -10 - 20 °C

With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; titanium(IV) tetraethanolate; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; 10 wt% Pd(OH)2 on carbon; water; hydrogen; tin(IV) chloride; sodium hydride; sodium carbonate; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

upstream raw materials:

tert-butyl ((2R,3R,4S,5R)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-3-yl)carbamate

N-[P-pentafluorophenyl-P-phenyl]-L-alanine isopropyl ester

D-Ribose

methyl α-D-ribofuranoside

Downstream raw materials:

(2S)-isopropyl 2-(((((2R,3S,4R,5R)-4-amino-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate