(R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

Base Information

• Chemical Name: (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid
• CAS No.: 119706-75-1
• Molecular Formula: C₂₀H₃₃NO₅Si
• Molecular Weight: 395.571

Synonyms:(R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

Chemical Property of (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

Chemical Property:

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Technology Process of (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

There total 4 articles about (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid 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: 72.0%

N-(tert-butoxycarbonyl)-D-tyrosine (70642-86-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid (119706-75-1)

Guidance literature:

N-(tert-butoxycarbonyl)-D-tyrosine; tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;

With potassium carbonate; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00245

Reference yield:

C26H47NO5Si2 (1026674-17-8) → (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid (119706-75-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; water; for 1h;

DOI:10.1016/S0040-4039(00)80460-8

Reference yield:

N-(tert-butoxycarbonyl)-D-tyrosine (70642-86-3) → (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid (119706-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 48 h

2: potassium carbonate / H₂O; methanol; tetrahydrofuran / 1 h

With 1H-imidazole; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80460-8

upstream raw materials:

C₂₆H₄₇NO₅Si₂

N-(tert-butoxycarbonyl)-D-tyrosine

tert-butyldimethylsilyl chloride

Downstream raw materials:

(S)-2-((R)-3-[3-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-{[(S)-2-((E)-(2S,6R,8S)-8-methoxymethoxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid tert-butyl ester

(S)-2-[(R)-3-[3-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-propionic acid tert-butyl ester

(S)-2-{(R)-3-[3-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-methylamino-propionylamino}-propionic acid tert-butyl ester

3-bromo-O-tert-butyldimethylsilyl-N-methyl-N-t-BOC-D-tyrosine

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