(9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate

Base Information

• Chemical Name: (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate
• CAS No.: 68802-90-4
• Molecular Formula: C₂₉H₃₉N₃O₇
• Molecular Weight: 541.645

Synonyms:(9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate

Chemical Property of (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate

Chemical Property:

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Technology Process of (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate

There total 6 articles about (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate 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: 80.0%

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate (68802-90-4)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2011.11.089

Reference yield: 62.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) → (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate (68802-90-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acsmedchemlett.8b00062

Reference yield:

N-t-Butyloxycarbonyl-L-phenylalanine-4,6-dimethylpyrimidin-2-yl thiol ester + (S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) + sodium hydrogencarbonate (144-55-8) → (9S,12S)-methyl 12-benzyl-16,16-dimethyl-3,11,14-trioxo-1-phenyl-2,15-dioxa-4,10,13-triazaheptadecane-9-carboxylate (68802-90-4)

Guidance literature:

With hydrogenchloride; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

sodium hydrogencarbonate

Downstream raw materials:

Boc-Phe-L-Lys(Z)-OH

benzyl ((S)-6-amino-5-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)-6-oxohexyl)carbamate

C₂₈H₃₈N₄O₇

C₄₉H₆₄N₆O₉S

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