e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron letters

Improved protection and esterification of a precursor of the taxotere® and taxol side chains

A Commerçon, D Bézard, F Bernard, JD Bourzat

Index: Commercon; Bezard; Bernard; Bourzat Tetrahedron Letters, 1992 , vol. 33, # 36 p. 5185 - 5188

Full Text: HTML

Citation Number: 142

Abstract

Abstract (4S, 5R)-N-BOC-2, 2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a, b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere® and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere®, taxol and analogs.

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~96%

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

10-Deacetylbaccatin III Structure

10-Deacetylbacc...

2,2,2-Trichlorethoxycarbonyl chloride Structure

2,2,2-Trichlore...

~71%

7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Baccatin III Structure

7-{[(2,2,2,-Tri...

7-O-(Triethylsilyl)-10-deacetyl Baccatin III Structure

7-O-(Triethylsi...

~%

7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Baccatin III Structure

7-{[(2,2,2,-Tri...

7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Baccatin III Structure

7-{[(2,2,2,-Tri...

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid Structure

(4S,5R)-3-(tert...

~10%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

Benzaldehyde Structure

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

10-Deacetylbaccatin III Structure

10-Deacetylbacc...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

7-O-(Triethylsilyl)-10-deacetyl Baccatin III Structure

7-O-(Triethylsi...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

~%

13-{[(3-t-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-7-O-(2,2,2-trichloroethyl)oxy]carbonyl) Baccatin III Structure

13-{[(3-t-Boc)-...

2-methyoxypropene Structure

2-methyoxypropene

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

~96%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

Benzaldehyde Structure

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

~%

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

Benzaldehyde Structure

~%

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

7-Troc-Paclitaxel Structure

7-Troc-Paclitaxel

~87%

Paclitaxel Structure

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

~88%

7,10-di-Troc-Docetaxel Structure

7,10-di-Troc-Do...

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

~73%

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

~%

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

Benzaldehyde Structure

~%

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~%

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

13-{[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl}-10-deacetyl-7,10-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Baccatin III Structure

13-{[(3-N-Boc)-...

~77%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

Benzaldehyde Structure

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester Structure

N-(t-Boc)-3-phe...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid Structure

(4S,5R)-3-(tert...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

3-(t-Boc)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl]formic Acid Ethyl Ester Structure

3-(t-Boc)-2,2-d...

~%

N-Des-t-boc-10-deacetyl-7,10-O-bis{[(2,2,2-trichloroethyl)oxy]carbonyl} Docetaxel Structure

N-Des-t-boc-10-...

Ethyl 3-Azido-2-hydroxy-propionate Structure

Ethyl 3-Azido-2...

~87%

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

Benzaldehyde Structure

~%

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate Structure

(2S,3R)-ethyl 3...

~%

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

(4S,5R)-3-((2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one Structure

(4S,5R)-3-((2S,...

~%

(2R,3S)-3-Phenylisoserine ethyl ester Structure

(2R,3S)-3-Pheny...

A simple and efficient method for regioselective and stereos...

[Nandanan; Phukan, Prodeep; Sudalai Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 3 p. 283 - 286]

A simple and efficient method for regioselective and stereos...

[Nandanan; Phukan, Prodeep; Sudalai Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 3 p. 283 - 286]

Chemo-enzymatic synthesis of all isomeric 3-phenylserines an...

[Hoenig, H.; Seufer-Wasserthal, P.; Weber, H. Tetrahedron, 1990 , vol. 46, # 11 p. 3841 - 3850]

A simple and efficient method for regioselective and stereos...

[Nandanan; Phukan, Prodeep; Sudalai Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 3 p. 283 - 286]

A simple and efficient method for regioselective and stereos...

[Nandanan; Phukan, Prodeep; Sudalai Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999 , vol. 38, # 3 p. 283 - 286]