(S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine

Base Information

• Chemical Name: (S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine
• CAS No.: 301530-18-7
• Molecular Formula: C₂₅H₂₅NO₆
• Molecular Weight: 435.477
• Mol file: 301530-18-7.mol

Synonyms:(S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine

Chemical Property of (S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine

There total 1 articles about (S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine 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: 71.0%

(S)-N-(benzyloxycarbonyl)-1-(3-benzyloxy-5-methoxy-4-methylphenyl)-2-hydroxyethylamine (301530-17-6) → (S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine (301530-18-7)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; In sodium hydrogencarbonate; acetone; at 0 ℃; for 2.5h;

DOI:10.1021/ol000180h

Reference yield:

(S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine (301530-18-7) → (R)-2-[(S)-2-Amino-2-(3-hydroxy-5-methoxy-4-methyl-phenyl)-acetylamino]-2-(3,5-dihydroxy-4-methoxy-phenyl)-N-methyl-acetamide (1026383-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 mg / HOAt; EDCI; TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

2: H₂; aq. HCl / Pd/C / methanol; tetrahydrofuran / 20 h / 760.05 Torr

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrogenolysis;

DOI:10.1021/ol000180h

Reference yield:

(S)-N-(benzyloxycarbonyl)-(3-benzyloxy-5-methoxy-4-methylphenyl)-glycine (301530-18-7) → [15-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-11-(3-hydroxy-5-methoxy-4-methyl-phenyl)-4-methoxy-8-methylcarbamoyl-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.13,7]heneicosa-1(19),3,5,7(21),16(20),17-hexaen-14-yl]-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1.1: 70 mg / HOAt; EDCI; TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

2.1: H₂; aq. HCl / Pd/C / methanol; tetrahydrofuran / 20 h / 760.05 Torr

3.1: HATU; TMP / dimethylformamide / 22 h / 0 - 20 °C

3.2: Cs₂CO₃ / dimethylformamide / 4 h / 20 °C

3.3: acetonitrile / 24 h / 20 °C / Photolysis

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Hydrogenolysis / 3.1: Acylation / 3.2: Cyclization / 3.3: demetalation;

DOI:10.1021/ol000180h

upstream raw materials:

(S)-N-(benzyloxycarbonyl)-1-(3-benzyloxy-5-methoxy-4-methylphenyl)-2-hydroxyethylamine

Downstream raw materials:

N-methyl (2R)-2-[(S)-1-[((benzyloxy)carbonyl)amino]-1-(3-benzyloxy-5-methoxy-4-methylphenyl)methylcarboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanamide

(R)-2-[(S)-2-Amino-2-(3-hydroxy-5-methoxy-4-methyl-phenyl)-acetylamino]-2-(3,5-dihydroxy-4-methoxy-phenyl)-N-methyl-acetamide