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

Base Information

• Chemical Name: O^ω-<(2S,2R)-2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-3-(4-morpholino)propyl>-N^α-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester
• CAS No.: 135912-87-7
• Molecular Formula: C₄₂H₆₅N₃O₁₂
• Molecular Weight: 803.991

Synonyms:

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

Chemical Property:

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

There total 2 articles about O^ω-<(2S,2R)-2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-3-(4-morpholino)propyl>-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: 56.0%

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid (121533-54-8) + Z-Glu<(2S,2R)-2-hydroxy-3-(4-morpholino)propyl>-OtBu (135912-86-6) → Oω-<(2S,2R)-2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-3-(4-morpholino)propyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (135912-87-7,135970-57-9)

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-<(2S,2R)-2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-3-(4-morpholino)propyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (135912-87-7,135970-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

2: 75 percent / alumina / diethyl ether

3: 56 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

With dmap; aluminum oxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In diethyl ether; dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

Oω-<(2S,2R)-2-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-3-(4-morpholino)propyl>-Nα-<(phenylmethoxy)carbonyl>-L-glutamic acid, 1,1-dimethylethyl ester (135912-87-7,135970-57-9) → (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-[2-((4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-5-carbonyloxy)-3-morpholin-4-yl-propyl] ester

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Ambient temperature;

DOI:10.1021/jm00099a004

upstream raw materials:

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

Z-Glu<(2S,2R)-2-hydroxy-3-(4-morpholino)propyl>-OtBu

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

Downstream raw materials:

(6R,7S,10S)-10-Amino-7-cyclohexylmethyl-6-hydroxy-3-morpholin-4-ylmethyl-1,4-dioxa-8-aza-cyclotridecane-5,9,13-trione

(8S,11S,12R)-2-butyl-11-(cyclohexylmethyl)-12-hydroxy-2-(4-morpholinomethyl)-8-<<(phenylmethoxy)carbonyl>amino>-5,9,13-trioxo-1,4-dioxa-10-azacyclotridecane

(8S,11S,12R)-11-(cyclohexylmethyl)-12-hydroxy-2-(4-morpholinomethyl)-8--L-phenylalanyl>-5,9,13-trioxo-1,4-dioxa-10-azacyclotridecane

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