3-Oxazolidinecarboxylic acid, 4-[4-[3-[4-(ethoxycarbonyl)-2-thiazolyl]-6-formyl-2-pyridinyl]-2-oxazolyl]-2 ,2-dimethyl-, phenylmethyl ester, (4S)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[4-[3-[4-(ethoxycarbonyl)-2-thiazolyl]-6-formyl-2-pyridinyl]-2-oxazolyl]-2 ,2-dimethyl-, phenylmethyl ester, (4S)-
• CAS No.: 666215-58-3
• Molecular Formula: C28H26N4O7S
• Molecular Weight: 562.603

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[4-[3-[4-(ethoxycarbonyl)-2-thiazolyl]-6-formyl-2-pyridinyl]-2-oxazolyl]-2 ,2-dimethyl-, phenylmethyl ester, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[4-[3-[4-(ethoxycarbonyl)-2-thiazolyl]-6-formyl-2-pyridinyl]-2-oxazolyl]-2 ,2-dimethyl-, phenylmethyl ester, (4S)-

There total 10 articles about 3-Oxazolidinecarboxylic acid, 4-[4-[3-[4-(ethoxycarbonyl)-2-thiazolyl]-6-formyl-2-pyridinyl]-2-oxazolyl]-2 ,2-dimethyl-, phenylmethyl ester, (4S)- 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: 65.0%

(S)-4-{2-Bromo-1-[6-dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-1-methoxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (666215-56-1) → (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester (666215-58-3)

Guidance literature:

With camphor-10-sulfonic acid; In toluene;

DOI:10.3987/COM-03-S27

Reference yield:

2-(6-Dimethoxymethyl-2-trifluoromethanesulfonyloxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (214040-92-3) → (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester (666215-58-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 96 percent / LiCl; Pd(PPh₃)4 / tetrahydrofuran

2.1: 90 percent / OsO₄; N-methylmorpholine N-oxide / CHCl₃

3.1: Et₃N

4.1: Et₃N

5.1: NaN₃ / dimethylformamide

6.1: H₂ / 10 percent Pd-C / methanol

6.2: 89 percent / diphenyl phosphorazidate; Et₃N

7.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran

8.1: Et₃N

8.2: 64 percent / DBU / CHCl₃

9.1: 71 percent / NBS

10.1: 65 percent / camphorsulfonic acid / toluene

With N-Bromosuccinimide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.3987/COM-03-S27

Reference yield:

2-(6-dimethoxymethyl-2-vinyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester (666215-49-2) → (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester (666215-58-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / OsO₄; N-methylmorpholine N-oxide / CHCl₃

2.1: Et₃N

3.1: Et₃N

4.1: NaN₃ / dimethylformamide

5.1: H₂ / 10 percent Pd-C / methanol

5.2: 89 percent / diphenyl phosphorazidate; Et₃N

6.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran

7.1: Et₃N

7.2: 64 percent / DBU / CHCl₃

8.1: 71 percent / NBS

9.1: 65 percent / camphorsulfonic acid / toluene

With N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.3987/COM-03-S27

upstream raw materials:

(S)-4-{2-Bromo-1-[6-dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-1-methoxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

2-(6-Dimethoxymethyl-2-trifluoromethanesulfonyloxy-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-(6-dimethoxymethyl-2-vinyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-[2-(1,2-dihydroxy-ethyl)-6-dimethoxymethyl-pyridin-3-yl]-thiazole-4-carboxylic acid ethyl ester

Downstream raw materials:

(S)-4-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester

2-{2-[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazol-4-yl]-6-dimethoxymethyl-pyridin-3-yl}-thiazole-4-carboxylic acid ethyl ester

2-(2-{2-[1-amino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxazol-4-yl}-6-dimethoxymethyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

2-(2-{2-[1-benzyloxycarbonylamino-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-oxazol-4-yl}-6-dimethoxymethyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester

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