(R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate

Base Information

• Chemical Name: (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate
• CAS No.: 1423040-36-1
• Molecular Formula: C₄₅H₆₁N₅O₉S
• Molecular Weight: 848.073
• Mol file: 1423040-36-1.mol

Synonyms:

Chemical Property of (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate

There total 18 articles about (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate 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:

4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester (943218-34-6) + (R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid (28697-07-6,28697-09-8,28697-11-2,71170-88-2) → (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate (1423040-36-1)

Guidance literature:

(R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid; With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; for 0.5h; Cooling with ice;

4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester; In dichloromethane; at 20 ℃;

DOI:10.1002/cjoc.201200984

Reference yield:

5-benzyl-3-methylenepyrrolidin-2-one → (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate (1423040-36-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine; dmap / dichloromethane / 24 h / 20 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 760.05 Torr

3.1: lithium hydroxide; water / tetrahydrofuran / 3 h / 20 °C

4.1: diethyl ether / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Cooling with ice

6.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.08 h

6.2: 24 h / 0 - 20 °C

7.1: pyridine / 12 h

8.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 °C

9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

10.1: hydrogenchloride / 1,4-dioxane / 2 h / Cooling with ice

11.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.5 h / Cooling with ice

11.2: 20 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; palladium 10% on activated carbon; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/cjoc.201200984

Reference yield:

(S)-2-methyl N-((R)-2-methylhex-5-en-3-yl)propane-2-sulfinamide (1072804-64-8) → (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate (1423040-36-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / Cooling with ice

2.1: water / 20 °C / Alkaline conditions

3.1: osmium(VIII) oxide; 4-methyl-morpholine / water; acetone / 34 h / 20 - 40 °C

4.1: sodium periodate / tetrahydrofuran; water / 0 - 20 °C

5.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.17 h / -78 °C

5.2: 2.5 h / -78 - 20 °C

6.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 °C

7.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.08 h

7.2: 24 h / 0 - 20 °C

8.1: pyridine / 12 h

9.1: hydrogenchloride / 1,4-dioxane / 2 h / 0 °C

10.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C

11.1: hydrogenchloride / 1,4-dioxane / 2 h / Cooling with ice

12.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 0.5 h / Cooling with ice

12.2: 20 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; boron trifluoride diethyl etherate; water; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/cjoc.201200984

upstream raw materials:

(S)-2-methyl N-((R)-2-methylhex-5-en-3-yl)propane-2-sulfinamide

(R)-tert-butyl (2-methylhex-5-en-3-yl)carbamate

methyl 2-{(1R,3R)-1-acetoxy-3-[(tert-butoxycarbonyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylate

2-{(1R,3R)-3-[(tert-butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl}-1,3-thiazole-4-carboxylic acid

Downstream raw materials:

methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-{[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate

C₃₇H₅₅N₅O₇S