3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide

Base Information

• Chemical Name: 3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide
• CAS No.: 160054-27-3
• Molecular Formula: C₅₃H₆₅N₉O₉S₃
• Molecular Weight: 1068.35
• Mol file: 160054-27-3.mol

Synonyms:3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide

Chemical Property of 3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide

There total 19 articles about 3-<2'-(2'''-((N-(4''(R)-((N^α((tert-butyloxy)carbonyl)-N^im(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide 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: 56.0%

(2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid (160054-25-1) + (2''S,3''S,4''R)-3-<2'-(2'''-((N-(4''-amino-3''-hydroxy-2''-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide hydrochloride → 3-<2'-(2'''-((N-(4''(R)-((Nα((tert-butyloxy)carbonyl)-Nim(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide (160054-27-3)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 23 ℃; for 56h;

DOI:10.1021/ja00092a011

Reference yield:

(2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester (141243-34-7) → 3-<2'-(2'''-((N-(4''(R)-((Nα((tert-butyloxy)carbonyl)-Nim(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide (160054-27-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / H₂S / methanol; H₂O / 48 h / 25 °C

2: 100 percent / tetrahydrofuran; H₂O / 1.5 h / 23 °C

3: 74 percent / 1 N aq. LiOH / tetrahydrofuran; methanol / 2 h / 0 °C

4: 56 percent / HOAt, NaHCO₃, DCC / dimethylformamide / 56 h / 23 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen sulfide; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00092a011

Reference yield:

(2S,3S,4R)-4-[[(tert-butoxy)carbonyl]amino]-3-hydroxy-2-methylpentanoic acid (73566-08-2) → 3-<2'-(2'''-((N-(4''(R)-((Nα((tert-butyloxy)carbonyl)-Nim(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)amino)-3''(S)-hydroxy-2''-(S)-methylpentanoyl)-L-threonyl)amino)ethyl)-2,4'-bithiazole-4-carboxamido>propyl methyl sulfide (160054-27-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / HOBt, NaHCO₃, EDCI / dimethylformamide / 24 h / 25 °C

2: 91 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C

3: 85 percent / HOBt, EDCI, NaHCO₃ / dimethylformamide / 50 h / 25 °C

4: 99 percent / 4 N HCl-EtOAc / 1 h / 23 °C

5: 56 percent / HOAt, NaHCO₃, DCC / dimethylformamide / 56 h / 23 °C

With hydrogenchloride; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja00092a011

upstream raw materials:

(2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

(2S,3S,4R)-4-[[(tert-butoxy)carbonyl]amino]-3-hydroxy-2-methylpentanoic acid

(S)-3-<(2S,3S,4R)-4--3-hydroxy-2-methylpentanoyl>-4-isopropyl-1,3-oxazolidin-2-one

(2S,3R)-2-Azido-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid methyl ester