O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate

Base Information

• Chemical Name: O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate
• CAS No.: 91229-95-7
• Molecular Formula: C₂₀H₂₇N₃O₅S₂
• Molecular Weight: 453.583

Synonyms:O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate

Chemical Property of O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate

Chemical Property:

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Technology Process of O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate

There total 9 articles about O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate 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: 71.0%

thiazolidine-2-thione (134469-06-0) + Oα-benzyl Nα-(tert-butyloxycarbonyl)-L-glutamic acid α-hydroxamate (91229-93-5) → Oα-benzyl Nα-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate (91229-95-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; for 12h; Ambient temperature;

DOI:10.1021/jo00193a016

Reference yield:

α-benzyl Nα-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamate (91229-92-4) → Oα-benzyl Nα-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate (91229-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / 5percent Pd/C / ethanol; H₂O / 12 h

2: 82 percent / NEt₃ / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 3h 2) r.t.

3: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 4 h / Ambient temperature

4: 71 percent / DCC / ethyl acetate / 12 h / Ambient temperature

With tetrabutyl ammonium fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00193a016

Reference yield:

α-benzyl Nα-(tert-butyloxycarbonyl)-L-glutamate (30924-93-7) → Oα-benzyl Nα-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate (91229-95-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 66 percent / pyridine / DCC / CH₂Cl₂ / 1) o deg C, 6h 2) r.t., overnight

2: 98 percent / H₂ / 5percent Pd/C / ethanol; H₂O / 12 h

3: 82 percent / NEt₃ / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 3h 2) r.t.

4: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 4 h / Ambient temperature

5: 71 percent / DCC / ethyl acetate / 12 h / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00193a016

upstream raw materials:

thiazolidine-2-thione

O^α-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamic acid α-hydroxamate

di-tert-butyl dicarbonate

N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamic acid

Downstream raw materials:

1-(benzyloxy)-3-<(tert-butyloxycarbonyl)amino>-2-piperidone

1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-piperidone

(4S)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-5-hydroxypentanamide

(S)-O-benzyl 2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanohydroxamate

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