(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

Base Information

Chemical Name:(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester
CAS No.:366785-43-5
Molecular Formula:C₁₁H₁₇NO₇
Molecular Weight:275.258
Hs Code.:

Synonyms:(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

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Chemical Property of (3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

Chemical Property:

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Technology Process of (3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

There total 1 articles about (3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-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:

: 1142-20-7
N-Cbz-Ala

: (3S,5R)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3,5-dimethyl ester

: (3S,5R)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

: 366785-43-5
(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

: 366785-37-7
2-[N-(carbobenzyloxy)-L-alanyl]-3(S),5(R)-di(carbomethoxy)oxazole

: (3R,5S)-2-((S)-2-Benzyloxycarbonylamino-propionyl)-isoxazolidine-3,5-dicarboxylic acid dimethyl ester

Guidance literature:: (3S,5R)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3,5-dimethyl ester; With sodium hydroxide; Chirazyme L-2; sodium phosphate; In water; toluene; for 8h; pH=7.6 - 7.8;

With hydrogenchloride; In ethyl acetate; at 0 ℃;

N-Cbz-Ala; With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; for 18h; Further stages.;
DOI:10.1021/jo010284l

Reference yield: 89.0%

: 962-39-0
L-Phenylalanine benzyl ester

: 366785-43-5
(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

: 366785-47-9
(3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In acetonitrile; for 10h;
DOI:10.1021/jo010284l

Reference yield:

: 366785-43-5
(3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester

: 366785-49-1
(3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / Et₃N; PyBOP / acetonitrile / 10 h

2: H₂ / Pd/C / methanol

3: 0.088 g / Et₃N; PyBOP / acetonitrile / 7 h

4: LiOH; H₂O / tetrahydrofuran / -10 - 20 °C

5: 0.066 g / Et₃N; PyBOP / acetonitrile / 3 h

With lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/jo010284l