Chemical Conversion of Cyclic. ALPHA.-Amino Acids to Cyclic. ALPHA.-Aminophosphonic Acids.

M Kaname, H Mashige, S Yoshifuji

Index: Kaname; Mashige; Yoshifuji Chemical and Pharmaceutical Bulletin, 2001 , vol. 49, # 5 p. 531 - 536

Full Text: HTML

Citation Number: 19

Abstract

The oxidative decarboxylation of cyclic α-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb (OAc) 4] gave 2-hydroxy derivatives, which were transformed into the corresponding α-aminophosphonic acid esters by treatment of trialkyl

 Related Synthetic Route
H-DL-Pro-OH Structure

609-36-9

H-DL-Pro-OH

2,2,2-Trichlorethoxycarbonyl chloride Structure

17341-93-4

2,2,2-Trichlore...

~99%

1-[(2,2,2-TRICHLOROETHOXY)CARBONYL]-PYRROLIDINE-2-CARBOXYLIC ACID Structure

347386-09-8

1-[(2,2,2-TRICH...

H-DL-Pro-OH Structure

609-36-9

H-DL-Pro-OH

4-Nitrobenzyl chloroformate Structure

4457-32-3

4-Nitrobenzyl c...

~99%

1-[(4-NITROBENZYLOXY)CARBONYL]-PYRROLIDINE-2-CARBOXYLIC ACID Structure

347386-12-3

1-[(4-NITROBENZ...

Boc-L-Proline Structure

15761-39-4

Boc-L-Proline

~65%

N-boc prrolidin-2-ol Structure

84766-91-6

N-boc prrolidin-2-ol

Z-Pro-OH Structure

1148-11-4

Z-Pro-OH

~93%

benzyl 2-hydroxypyrrolidine-1-carboxylate Structure

69261-54-7

benzyl 2-hydrox...

1-benzyl 2-(4-nitrobenzyl) pyrrolidine-1,2-dicarboxylate Structure

98782-97-9

1-benzyl 2-(4-n...

~89%

benzyl 2-hydroxypyrrolidine-1-carboxylate Structure

69261-54-7

benzyl 2-hydrox...

1-benzyl 2-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate Structure

78816-93-0

1-benzyl 2-(2,5...

~61%

benzyl 2-hydroxypyrrolidine-1-carboxylate Structure

69261-54-7

benzyl 2-hydrox...

Benzyl 2-hydroxy-1-piperidinecarboxylate Structure

69622-67-9

Benzyl 2-hydrox...

~%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...

Benzoyl chloride Structure

98-88-4

Benzoyl chloride

H-DL-Pro-OH Structure

609-36-9

H-DL-Pro-OH

~99%

1-benzoylpyrrolidine-2-carboxylic acid Structure

195719-48-3

1-benzoylpyrrol...

N-Cbz-2-Piperidinecarboxylic acid Structure

28697-07-6

N-Cbz-2-Piperid...

~%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...

Pipecolic acid Structure

4043-87-2

Pipecolic acid

~%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...

benzyl 2-(dimethoxyphosphoryl)piperidine-1-carboxylate Structure

347386-51-0

benzyl 2-(dimet...

~%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...

tert-butyl 2-(dimethoxyphosphoryl)piperidine-1-carboxylate Structure

347386-54-3

tert-butyl 2-(d...

~97%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...

2,2,2-trichloroethyl 2-(dimethoxyphosphoryl)piperidine-1-carboxylate Structure

347386-45-2

2,2,2-trichloro...

~%

piperidin-2-ylphosphonic acid Structure

106647-45-4

piperidin-2-ylp...


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