Bulletin of the Chemical Society of Japan

The steric hindrance of the stepwise reaction of N-carboxy. ALPHA.-amino acid anhydride with the. ALPHA.-amino acid ester.

M Oya, T Takahashi

Index: Oya, Masanao; Takahashi, Tomoko Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 9 p. 2705 - 2707

Full Text: HTML

Citation Number: 7

Abstract

The mechanisms of the reactions of 4-alkyloxazolidinediones (1)(N-carboxy α-amino acid anhydrides (NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures. Two types of reactions were observed:(1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide benzyl esters (4) were ...

 Related Synthetic Route
N/A Structure

74939-28-9

N/A

~%

H-Val-Gly-OH Structure

686-43-1

H-Val-Gly-OH

L-Valyl-L-valine benzyl ester Structure

101222-19-9

L-Valyl-L-valin...

~%

H-Val-Val-OH Structure

3918-94-3

H-Val-Val-OH

L-Valine benzyl ester p-toluenesulfonate salt Structure

16652-76-9

L-Valine benzyl...

~%

H-Val-Val-OH Structure

3918-94-3

H-Val-Val-OH

(4S)-4-Isopropyl-1,3-oxazolidine-2,5-dione Structure

24601-74-9

(4S)-4-Isopropy...

~%

H-Val-Val-OH Structure

3918-94-3

H-Val-Val-OH

N/A Structure

47094-07-5

N/A

~%

D-Alanine, N-D-valyl-(9CI) Structure

1115-74-8

D-Alanine, N-D-...

(4S)-4-Isopropyl-1,3-oxazolidine-2,5-dione Structure

24601-74-9

(4S)-4-Isopropy...

~%

D-Alanine, N-D-valyl-(9CI) Structure

1115-74-8

D-Alanine, N-D-...

N/A Structure

136554-62-6

N/A

~%

H-VAL-LEU-OH Structure

3989-97-7

H-VAL-LEU-OH

H-Leu-OBzl.TosOH Structure

1738-77-8

H-Leu-OBzl.TosOH

~%

H-VAL-LEU-OH Structure

3989-97-7

H-VAL-LEU-OH

(4S)-4-Isopropyl-1,3-oxazolidine-2,5-dione Structure

24601-74-9

(4S)-4-Isopropy...

~%

H-VAL-LEU-OH Structure

3989-97-7

H-VAL-LEU-OH

(S)-benzyl 2-((S)-2-amino-3-phenylpropanamido)-3-methylbutanoate Structure

108050-48-2

(S)-benzyl 2-((...

~%

H-Phe-Val-OH Structure

3918-90-9

H-Phe-Val-OH

H-Phe-Ala-OBn Structure

73393-25-6

H-Phe-Ala-OBn

~%

Phe-Ala Structure

3918-87-4

Phe-Ala

(s)-(-)-4-benzyloxazolidine-2,5-dione Structure

14825-82-2

(s)-(-)-4-benzy...

~%

Phe-Ala Structure

3918-87-4

Phe-Ala

L-leucyl-L-valine benzyl ester Structure

84111-39-7

L-leucyl-L-vali...

~%

Leu-Val-OH Structure

13588-95-9

Leu-Val-OH

L-Valine benzyl ester p-toluenesulfonate salt Structure

16652-76-9

L-Valine benzyl...

~%

Leu-Val-OH Structure

13588-95-9

Leu-Val-OH

(S)-(-)-4-Isobutyloxazolidine-2,5-Dione Structure

3190-70-3

(S)-(-)-4-Isobu...

~%

Leu-Val-OH Structure

13588-95-9

Leu-Val-OH

(S,S)-2-(2-amino-3-phenylpropionylamino)acetic acid benzyl ester Structure

94779-07-4

(S,S)-2-(2-amin...

~%

H-Phe-Gly-OH Structure

721-90-4

H-Phe-Gly-OH

(s)-(-)-4-benzyloxazolidine-2,5-dione Structure

14825-82-2

(s)-(-)-4-benzy...

~%

H-Phe-Gly-OH Structure

721-90-4

H-Phe-Gly-OH


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