(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

Base Information

• Chemical Name: (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
• CAS No.: 135912-88-8
• Molecular Formula: C₃₀H₄₃N₃O₉
• Molecular Weight: 589.686

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-[2-((4S,5R)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-5-carbonyloxy)-3-morpholin-4-yl-propyl] ester → (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 (135912-88-8,143614-91-9,143678-54-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; for 144h; Yield given; Ambient temperature;

DOI:10.1021/jm00099a004

Reference yield:

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → (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 (135912-88-8,143614-91-9,143678-54-0)

Guidance literature:

Multi-step reaction with 5 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

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

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

With 4-methyl-morpholine; dmap; aluminum oxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-tert-butyl ester 5-oxiranylmethyl ester (135912-85-5) → (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 (135912-88-8,143614-91-9,143678-54-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / alumina / diethyl ether

2: 56 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

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

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

With 4-methyl-morpholine; dmap; aluminum oxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm00099a004

upstream raw materials:

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

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-tert-butyl ester 5-oxiranylmethyl ester

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

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

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

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