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

Base Information

• Chemical Name: O^ω-<2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>ethyl>-N^α-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester
• CAS No.: 143508-43-4
• Molecular Formula: C₃₇H₅₆N₂O₁₁
• Molecular Weight: 704.858

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

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

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

There total 2 articles about O^ω-<2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>ethyl>-N^α-<(phenylmethoxy)carbonyl>-L-glutamic acid, 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: 100.0%

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid (121533-54-8) + Z-Glu(2-hydroxyethyl)-OtBu (143508-40-1) → Oω-<2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>ethyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (143508-43-4)

Guidance literature:

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

DOI:10.1021/jm00099a004

Reference yield:

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → Oω-<2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>ethyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (143508-43-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

2: 100 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

Oω-<2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>ethyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (143508-43-4) → (6R,7S,10S)-10-Amino-7-cyclohexylmethyl-6-hydroxy-1,4-dioxa-8-aza-cyclotridecane-5,9,13-trione (1054648-71-3)

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:

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid

Z-Glu(2-hydroxyethyl)-OtBu

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt

Downstream raw materials:

(6R,7S,10S)-10-Amino-7-cyclohexylmethyl-6-hydroxy-1,4-dioxa-8-aza-cyclotridecane-5,9,13-trione

(8S,11S,12R)-11-(cyclohexylmethyl)-12-hydroxy-8-<<(phenylmethoxy)carbonyl>amino>-5,9,13-trioxo-1,4-dioxa-10-azacyclotridecane

(8S,11S,12R)-11-(cyclohexylmethyl)-8--L-phenylalanyl>-12-hydroxy-5,9,13-trioxo-1,4-dioxa-10-azacyclotridecane

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