O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester

Base Information

• Chemical Name: O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester
• CAS No.: 137238-57-4
• Molecular Formula: C₃₈H₅₈N₂O₁₁
• Molecular Weight: 718.885

Synonyms:O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester

Chemical Property of O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester

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Technology Process of O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester

There total 2 articles about O^ω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester 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:

5-oxo-5-(phenylmethoxy)pentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarboxylate (134848-93-4) → Oω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-Nα-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester (137238-57-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / methanol / 760 Torr

2: 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

With dmap; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7) + (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-carboxy-butyl) ester (137238-58-5) → Oω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-Nα-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester (137238-57-4)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; Yield given;

DOI:10.1021/jm00099a004

Reference yield:

Oω-<5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>pentanoyl>-Nα-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester (137238-57-4) → (3R,4S,7S)-7-Amino-4-cyclohexylmethyl-3-hydroxy-1,9-dioxa-5-aza-cyclotetradecane-2,6,10-trione

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

2: N-methylmorpholine, hydroxybenzotriazole (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran / 144 h / Ambient temperature

3: H₂ / 10 percent Pd/C / methanol / 760 Torr

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00099a004

upstream raw materials:

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-carboxy-butyl) ester

5-oxo-5-(phenylmethoxy)pentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarboxylate

Downstream raw materials:

(9S,12S,13R)-12-(cyclohexylmethyl)-13-hydroxy-9-<<(phenylmethoxy)carbonyl>amino>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

(9S,12S,13R)-12-(cyclohexylmethyl)-13-hydroxy-9--L-phenylalanyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

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