L-Tyrosine, N-[(2S,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-oxopentyl ]-3-iodo-O-(methoxymethyl)-, methyl ester

Base Information

• Chemical Name: L-Tyrosine, N-[(2S,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-oxopentyl ]-3-iodo-O-(methoxymethyl)-, methyl ester
• CAS No.: 602301-44-0
• Molecular Formula: C24H40INO6Si
• Molecular Weight: 593.575
• Mol file: 602301-44-0.mol

Synonyms:

Chemical Property of L-Tyrosine, N-[(2S,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-oxopentyl ]-3-iodo-O-(methoxymethyl)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Tyrosine, N-[(2S,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-oxopentyl ]-3-iodo-O-(methoxymethyl)-, methyl ester

There total 4 articles about L-Tyrosine, N-[(2S,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methyl-1-oxopentyl ]-3-iodo-O-(methoxymethyl)-, 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: 88.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-2-((2S,3S)-2-Hydroxy-3-methyl-pentanoylamino)-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester (602301-48-4) → (S)-2-[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester (602301-44-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.200351130

Reference yield:

(2S,3S)-2-Hydroxy-3-methylpentanoic acid (488-15-3,59653-35-9,70748-47-9,86540-81-0,86630-77-5,51576-04-6) → (S)-2-[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester (602301-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 0 °C

2: 85 percent / K₂CO₃ / acetone

3: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.200351130

Reference yield:

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride (79677-58-0,122908-62-7) → (S)-2-[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester (602301-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 0 °C

2: 85 percent / K₂CO₃ / acetone

3: 88 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.200351130

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-2-((2S,3S)-2-Hydroxy-3-methyl-pentanoylamino)-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester

(2S,3S)-2-Hydroxy-3-methylpentanoic acid

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride

Downstream raw materials:

(S)-2-[(2S,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-3-[4-methoxymethoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

TMC-95A

3-(3-{3-[5-benzyloxycarbonylamino-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl}-4-methoxymethoxy-phenyl)-2-[2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-propionic acid methyl ester

(S)-2-{(S)-3-(3-{(S)-3-[(2R,4R,5R)-5-Amino-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl}-4-methoxymethoxy-phenyl)-2-[(2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentanoylamino]-propionylamino}-butaoic acid