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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者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

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

全文：HTML全文

被引用次数: 142

摘要

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结构式

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

~96%

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

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

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

~%

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

10-脱乙酰基巴卡丁 III； 10-去乙酰基巴卡亭结构式

10-脱乙酰基巴卡丁 III；...

氯甲酸-2,2,2-三氯乙酯结构式

氯甲酸-2,2,2-三氯乙酯

~71%

7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

7-O-(Triethylsilyl)-10-deacetyl Baccatin III结构式

7-O-(Triethylsi...

~%

7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

7-O-(2,2,2-三氯乙氧基羰基)浆果赤霉素 III结构式

7-O-(2,2,2-三氯乙氧...

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

(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结构式

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

Ethyl 3-Azido-2-hydroxy-propionate结构式

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结构式

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

苯甲醛结构式

~%

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结构式

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

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate结构式

(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结构式

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

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

(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结构式

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

10-脱乙酰基巴卡丁 III； 10-去乙酰基巴卡亭结构式

10-脱乙酰基巴卡丁 III；...

~%

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结构式

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

二碳酸二叔丁酯结构式

二碳酸二叔丁酯

~%

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结构式

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

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

~%

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结构式

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

7-O-(Triethylsilyl)-10-deacetyl Baccatin III结构式

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结构式

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

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

~%

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结构式

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

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

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结构式

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

2-甲氧基丙烯结构式

2-甲氧基丙烯

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

~96%

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

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

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

~%

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

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

苯甲醛结构式

~%

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

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

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate结构式

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

~%

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

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

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

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

~%

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

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

二碳酸二叔丁酯结构式

二碳酸二叔丁酯

~%

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

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

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

~%

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

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

苯甲醛结构式

~%

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

7-(2,2,2-三氯乙基氧基羰基)紫杉醇结构式

7-(2,2,2-三氯乙基氧基...

~87%

紫杉醇结构式

二碳酸二叔丁酯结构式

二碳酸二叔丁酯

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

~88%

多西紫杉醇中间体结构式

多西紫杉醇中间体

二碳酸二叔丁酯结构式

二碳酸二叔丁酯

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

~73%

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

~%

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

苯甲醛结构式

~%

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate结构式

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

~%

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

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

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

~%

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

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结构式

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

~77%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

苯甲醛结构式

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate结构式

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

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

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

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

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

N-(t-Boc)-3-苯基异丝氨酸乙酯结构式

N-(t-Boc)-3-苯基异丝氨酸乙酯

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

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

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

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

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

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

~%

N-Des-t-boc-10-去乙酰基7,10-O-双{[((2,2,2-三氯乙基)氧基]羰基}多西他赛结构式

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

Ethyl 3-Azido-2-hydroxy-propionate结构式

Ethyl 3-Azido-2...

~87%

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

苯甲醛结构式

~%

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

(2S,3R)-ethyl 3-phenyloxirane-2-carboxylate结构式

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

~%

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

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

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

~%

(2R,3S)-3-苯基异丝氨酸乙酯结构式

(2R,3S)-3-苯基异丝氨酸乙酯

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]