2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid

Base Information

• Chemical Name: 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid
• CAS No.: 851127-31-6
• Molecular Formula: C₂₀H₂₄N₂O₆S
• Molecular Weight: 420.486
• Mol file: 851127-31-6.mol

Synonyms:2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid

Chemical Property of 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid

There total 9 articles about 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid 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: 63.0%

(1'R,3'R)-2-(1'-acetoxy-3'-benzyloxycarbonylamino-4'-methylpentyl)thiazole-4-carboxylic acid ethyl ester (796039-46-8) → 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid (851127-31-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 20h;

DOI:10.1021/ol048252i

Reference yield:

N-benzyloxycarbonyl-L-valinol (6216-65-5) → 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid (851127-31-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaBr; TEMPO; NaOCl / H₂O; toluene; ethyl acetate / 4 h / 0 °C

2.1: 3.9 g / CH₂Cl₂ / 14 h / 0 - 20 °C

3.1: 80 percent / rac-BINAP; t-BuONa; CuCl / polymethylhydrosiloxane / toluene / 72 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 66 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / tetrahydrofuran / 1 h / -78 °C

5.1: 77 percent / NH₃ / methanol / 14 h / -78 - 20 °C

6.1: 75 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

7.1: 86 percent / Belleau's reagent / tetrahydrofuran / 3 h / 0 °C

8.1: acetone / 1.5 h / -10 °C

8.2: 78 percent / pyridine; (CF₃CO)2O / CH₂Cl₂ / 3 h / -30 - 0 °C

9.1: 63 percent / NaOH / tetrahydrofuran; H₂O / 20 h / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; ammonia; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides; sodium bromide; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; 2.1: Wiitig olefination;

DOI:10.1021/ol048252i

Reference yield:

N-benzyloxycarbonyl-L-valinal (138754-84-4,95500-73-5) → 2-((1R,3R)-1-Acetoxy-3-benzyloxycarbonylamino-4-methyl-pentyl)-thiazole-4-carboxylic acid (851127-31-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 3.9 g / CH₂Cl₂ / 14 h / 0 - 20 °C

2.1: 80 percent / rac-BINAP; t-BuONa; CuCl / polymethylhydrosiloxane / toluene / 72 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 66 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / tetrahydrofuran / 1 h / -78 °C

4.1: 77 percent / NH₃ / methanol / 14 h / -78 - 20 °C

5.1: 75 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

6.1: 86 percent / Belleau's reagent / tetrahydrofuran / 3 h / 0 °C

7.1: acetone / 1.5 h / -10 °C

7.2: 78 percent / pyridine; (CF₃CO)2O / CH₂Cl₂ / 3 h / -30 - 0 °C

8.1: 63 percent / NaOH / tetrahydrofuran; H₂O / 20 h / 20 °C

With pyridine; sodium hydroxide; ammonia; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 1.1: Wiitig olefination;

DOI:10.1021/ol048252i

upstream raw materials:

(1'R,3'R)-2-(1'-acetoxy-3'-benzyloxycarbonylamino-4'-methylpentyl)thiazole-4-carboxylic acid ethyl ester

N-benzyloxycarbonyl-L-valinol

N-benzyloxycarbonyl-L-valinal

methyl (2R,4R)-4-<(benzyloxycarbonyl)amino>-2-hydroxy-5-methylhexanoate

Downstream raw materials:

(1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester

(1R,3R,1''R,3''S)-acetic acid 1-[4'-(1''-benzyl-4''-hydroxy-3''-methylbutylcarbamoyl)thiazol-2'-yl]-3-benzyloxycarbonylamino-4-methylpentyl ester

(1R,2'R,1'''R,3'''S)-[1-(2'-{4''-[1'''-benzyl-4'''-(tert-butyldiphenylsilanyloxy)-3'''-methylbutylcarbamoyl]thiazol-2''-yl}-2'-hydroxyethyl)-2-methylpropyl]carbamic acid benzyl ester