{N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate}

Base Information

• Chemical Name: {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate}
• CAS No.: 264198-18-7
• Molecular Formula: C₂₆H₃₈N₄O₉
• Molecular Weight: 550.609

Synonyms:{N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate}

Chemical Property of {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate}

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate}

There total 4 articles about {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate} 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:

BOC-glycine (4530-20-5) + (S)-3-{[(2R,5S)-5-((S)-1-Amino-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-2-benzyloxycarbonylamino-propionic acid methyl ester (294664-69-0) → {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate} (264198-18-7)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride (35761-27-4,96192-93-7) → {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate} (264198-18-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / HOBt; iPr₂NEt; EDC / tetrahydrofuran / 16 h / 20 °C

2: TFA / CH₂Cl₂ / 2 h / 20 °C

3: 350 mg / HOBt; EDC; iPr₂NEt / tetrahydrofuran / 18 h / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Deacylation / 3: Acylation;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

(2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid (259091-45-7) → {N-(tert-Butoxycarbonyl)glycyl}-{(2'R,5'S,1''S)-5'-(1''-aminoethyl)tetrahydrofuran-2'-carbonyl}-{(2S)-3-amino-2-benzyloxycarbonylamino methyl propionate} (264198-18-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / HOBt; iPr₂NEt; EDC / tetrahydrofuran / 16 h / 20 °C

2: TFA / CH₂Cl₂ / 2 h / 20 °C

3: 350 mg / HOBt; EDC; iPr₂NEt / tetrahydrofuran / 18 h / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Deacylation / 3: Acylation;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

upstream raw materials:

BOC-glycine

(S)-3-{[(2R,5S)-5-((S)-1-Amino-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-2-benzyloxycarbonylamino-propionic acid methyl ester

methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride

(2R,5S,1'S)-5-{1'-[(tert-butoxycarbonyl)amino]ethyl}tetrahydrofuran-2-carboxylic acid

Downstream raw materials:

C₃₂H₄₈N₆O₁₁

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