(R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester

Base Information

• Chemical Name: (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester
• CAS No.: 586413-61-8
• Molecular Formula: C₂₀H₃₃NO₅Si
• Molecular Weight: 395.571

Synonyms:(R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester

Chemical Property of (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester

Chemical Property:

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Technology Process of (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester

There total 2 articles about (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate (143323-49-3,141518-55-0) → (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester (586413-61-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 12h;

DOI:10.1021/ja030249r

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → (R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester (586413-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / Heating

2: aq. K₂CO₃ / dioxane / 4 h / 20 °C

3: triethylamine; DMAP / CH₂Cl₂ / 5 h / 50 °C

With dmap; thionyl chloride; potassium carbonate; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja049779t

Reference yield:

(R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycine methyl ester (586413-61-8) → amino-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acetic acid methyl ester (586413-53-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja030249r

upstream raw materials:

tert-butyldimethylsilyl chloride

(R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate

D-4-hydroxyphenylglycine

Downstream raw materials:

amino-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acetic acid methyl ester

(R)-N-(t-butoxycarbonyl)-4-(t-butyldimethylsiloxy)phenylglycinol

(R)-4-(4-hydroxyphenyl)-oxazolidin-2-one

(R)-{[(8R,11R,14S)-8-Amino-11-(3,5-dichloro-4-hydroxy-phenyl)-4-hydroxy-5-iodo-13-methyl-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester

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