S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate

Base Information

• Chemical Name: S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate
• CAS No.: 1274754-60-7
• Molecular Formula: C₁₈H₂₇NO₃S
• Molecular Weight: 337.483

Synonyms:S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate

Chemical Property of S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate

Chemical Property:

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Technology Process of S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate

There total 1 articles about S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate 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: 66.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 2-methylpropan-2-thiol (75-66-1) → S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate (1274754-60-7)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol1029723

Reference yield: 100.0%

3-mercaptopropionitrile (1001-58-7) + S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate (1274754-60-7) → N-Boc-Phe-S-2-cyanoethyl ester (1396174-63-2)

Guidance literature:

With 15-crown-5; sodium thiophenolate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol302247h

Reference yield:

piperidine (110-89-4) + S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate (1274754-60-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (S)-tert-butyl 1-(dimethylamino)-1-oxo-3-phenylpropan-2-ylcarbamate (78800-68-7) + (S)-tert-butyl (1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)carbamate (120125-43-1)

Guidance literature:

at 20 ℃; Kinetics;

DOI:10.1021/ol1029723

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

2-methylpropan-2-thiol

Downstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(S)-tert-butyl 1-(dimethylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

(S)-tert-butyl (1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)carbamate

S-[1,1-dimethyl-4-(trityloxy)butyl] (2S)-2-{[tert-butoxycarbonyl]amino}-3-phenylpropanethioate

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