Journal of Fluorine Chemistry

Asymmetric synthesis of fluorinated L-tyrosine and meta-L-tyrosines

M Monclus, C Masson, A Luxen

Index: Monclus, Michel; Masson, Carine; Luxen, Andre Journal of Fluorine Chemistry, 1995 , vol. 70, # 1 p. 39 - 44

Full Text: HTML

Citation Number: 10

Abstract

A convenient asymmetric synthesis of (2S)-2-amino-3-(2-fluoro-5-hydroxyphenyl) propanoic acid,(2S)-2-amino-3-(4-fluoro-3-hydroxyphenyl) propanoic acid and (2S)-2-amino-3-(2- fluoro-4-hydroxyphenyl) propanoic acid is described. Key steps include the synthesis of the benzyl bromides, the alkylation of the glycine enolate derivative ((S)-Boc-BMI) and the hydrolysis of the alkylated Boc-BMI.

 Related Synthetic Route
(4-Fluoro-3-methoxyphenyl)methanol Structure

128495-45-4

(4-Fluoro-3-met...

~84%

4-(Bromomethyl)-1-fluoro-2-methoxybenzene Structure

141080-73-1

4-(Bromomethyl)...

3-Fluorophenol Structure

372-20-3

3-Fluorophenol

~%

(2-Fluoro-4-methoxyphenyl)methanol Structure

405-09-4

(2-Fluoro-4-met...

2-Fluoro-4-hydroxybenzaldehyde Structure

348-27-6

2-Fluoro-4-hydr...

~%

(2-Fluoro-4-methoxyphenyl)methanol Structure

405-09-4

(2-Fluoro-4-met...

3-[(dimethyl-tert-butylsilyl)oxy]fluorobenzene Structure

114635-97-1

3-[(dimethyl-te...

~%

(2-Fluoro-4-methoxyphenyl)methanol Structure

405-09-4

(2-Fluoro-4-met...

(2-Fluoro-4-methoxyphenyl)methanol Structure

405-09-4

(2-Fluoro-4-met...

~93%

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

3-Fluorophenol Structure

372-20-3

3-Fluorophenol

~%

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

2-Fluoro-4-hydroxybenzaldehyde Structure

348-27-6

2-Fluoro-4-hydr...

~%

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

2-Fluoro-4-methoxybenzaldehyde Structure

331-64-6

2-Fluoro-4-meth...

~%

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

3-[(dimethyl-tert-butylsilyl)oxy]fluorobenzene Structure

114635-97-1

3-[(dimethyl-te...

~%

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

3-Fluorophenol Structure

372-20-3

3-Fluorophenol

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

2-Fluoro-4-hydroxybenzaldehyde Structure

348-27-6

2-Fluoro-4-hydr...

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

2-Fluoro-4-methoxybenzaldehyde Structure

331-64-6

2-Fluoro-4-meth...

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

(2-Fluoro-4-methoxyphenyl)methanol Structure

405-09-4

(2-Fluoro-4-met...

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

3-[(dimethyl-tert-butylsilyl)oxy]fluorobenzene Structure

114635-97-1

3-[(dimethyl-te...

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

1-(Bromomethyl)-2-fluoro-4-methoxybenzene Structure

54788-19-1

1-(Bromomethyl)...

~%

2-fluoro-L-tyrosine Structure

78709-81-6

2-fluoro-L-tyrosine

2-Fluoro-4-hydroxybenzaldehyde Structure

348-27-6

2-Fluoro-4-hydr...

methyl iodide Structure

74-88-4

methyl iodide

~85%

2-Fluoro-4-methoxybenzaldehyde Structure

331-64-6

2-Fluoro-4-meth...

2-fluoro-5-methoxybenzaldehyde Structure

105728-90-3

2-fluoro-5-meth...

~%

BENZENE, 2-(BROMOMETHYL)-1-FLUORO-4-METHOXY- Structure

91319-42-5

BENZENE, 2-(BRO...


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