(4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

Base Information

• Chemical Name: (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline
• CAS No.: 157770-69-9
• Molecular Formula: C₂₆H₂₈N₄O₃S₃
• Molecular Weight: 540.731

Synonyms:(4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

Chemical Property of (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

Chemical Property:

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Technology Process of (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

There total 10 articles about (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ²-thiazoline)-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline 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: 70.0%

(4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline (157770-59-7) + R-2-methylcysteine-5'-methyloxazole-4'-methyl ester hydrochloride → (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ2-thiazoline)-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline (157770-69-9)

Guidance literature:

With triethylamine; In methanol; for 48h; Heating;

DOI:10.1016/S0040-4039(00)77284-4

Reference yield: 55.0%

(-)-Thiangazole (138667-71-7,144370-38-7) → (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ2-thiazoline)-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline (157770-69-9) + 5-Methyl-2-[(4R,4'S,4''S)-4,4',4''-trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl]-oxazole-4-carboxylic acid (257278-40-3)

Guidance literature:

(-)-Thiangazole; With sodium acetate; dinitrogen tetraoxide; In dichloromethane; at -20 ℃; for 0.75h;

In chloroform; at 70 ℃;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3381::AID-EJOC3381>3.0.CO;2-W

Reference yield:

benzyltriphenylphosphonium chloride (1100-88-5) → (4S)-4-methyl-4'<2'(4'S)-4'-methyl-4'(2''-(4''R)-4''-methyl-4''-(2'''-(4'''-methoxycarbonyl-5'''-methyl)oxazole)-Δ2-thiazoline)-Δ2-thiazoline>-2-cinnamyl-Δ2-thiazoline (157770-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 36 percent / 50 percent NaOH / H₂O; CH₂Cl₂ / 0.5 h / 20 °C

2.1: N₂O₄; NaOAc / CH₂Cl₂ / 0.75 h / -20 °C

2.2: 55 percent / CHCl₃ / 70 °C

With sodium hydroxide; sodium acetate; dinitrogen tetraoxide; In dichloromethane; water; 1.1: Wittig reaction / 2.1: Nitrosation / 2.2: Rearrangement;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3381::AID-EJOC3381>3.0.CO;2-W

upstream raw materials:

(4S)-4-methyl-4-<2'(4'R)-4'-nitrile-4'-methyl-Δ²-thiazoline>-2-cinnamyl-Δ²-thiazoline

(-)-Thiangazole

benzyltriphenylphosphonium chloride

2-((4R,4'S,4''S)-2''-Formyl-4,4',4''-trimethyl-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl)-5-methyl-oxazole-4-carboxylic acid methylamide

Downstream raw materials:

5-Methyl-2-[(4R,4'S,4''S)-4,4',4''-trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl]-oxazole-4-carboxylic acid

{5-Methyl-2-[(4R,4'S,4''S)-4,4',4''-trimethyl-2''-((E)-styryl)-4,5,4',5',4'',5''-hexahydro-[2,4';2',4'']terthiazol-4-yl]-oxazol-4-yl}-methanol

(-)-Thiangazole

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