Journal of Organic Chemistry, volume 62, issue 11, pages 3440-3448

Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor

Pierre L Beaulieu ¹

Pierre Lavallée ¹

Abraham ¹

Paul C. Anderson ¹

Colette Boucher ¹

YVES BOUSQUET ¹

Jean-Simon Duceppe ¹

James Gillard ¹

Vida Gorys ¹

Chantal Grand-Maître ¹

Louis Grenier ¹

Yvan Guindon ¹

Ingrid Guse ¹

Louis Plamondon ¹

François Soucy ¹

Serge Valois ¹

Dominik Wernic ¹

Christiane Yoakim ¹

Show full list: 18 authors

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Bio-Méga Research Division, Boehringer Ingelheim (Canada) Ltd., 2100 Cunard Street, Laval (Québec), Canada, H7S 2G5 |

Publication type: Journal Article

Publication date: 1997-05-01

American Chemical Society (ACS)

Journal: Journal of Organic Chemistry

scimago Q2

SJR: 0.724

CiteScore: 6.2

Impact factor: 3.3

ISSN: 00223263, 15206904

DOI: 10.1021/jo9702655

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Organic Chemistry

Abstract

Palinavir is a potent peptidomimetic-based HIV protease inhibitor. We have developed a highly convergent and stereoselective synthesis which is amenable to the preparation of multikilogram quantities of this compound. The synthetic sequence proceeds in 24 distinct chemical steps (with several integrated, multistep operations) from commercially available starting materials. No chromatographies are required throughout the process, and the final product is purified by crystallization of its dihydrochloride salt to >99% homogeneity.

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70 Total citations

2 Recent citations

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Beaulieu P. L. et al. Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor // Journal of Organic Chemistry. 1997. Vol. 62. No. 11. pp. 3440-3448.

GOST all authors (up to 50) Copy

Beaulieu P. L., Lavallée P., Abraham, Anderson P. C., Boucher C., BOUSQUET Y., Duceppe J., Gillard J., Gorys V., Grand-Maître C., Grenier L., Guindon Y., Guse I., Plamondon L., Soucy F., Valois S., Wernic D., Yoakim C. Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor // Journal of Organic Chemistry. 1997. Vol. 62. No. 11. pp. 3440-3448.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jo9702655

UR - https://doi.org/10.1021/jo9702655

TI - Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor

T2 - Journal of Organic Chemistry

AU - Beaulieu, Pierre L

AU - Lavallée, Pierre

AU - Abraham

AU - Anderson, Paul C.

AU - Boucher, Colette

AU - BOUSQUET, YVES

AU - Duceppe, Jean-Simon

AU - Gillard, James

AU - Gorys, Vida

AU - Grand-Maître, Chantal

AU - Grenier, Louis

AU - Guindon, Yvan

AU - Guse, Ingrid

AU - Plamondon, Louis

AU - Soucy, François

AU - Valois, Serge

AU - Wernic, Dominik

AU - Yoakim, Christiane

PY - 1997

DA - 1997/05/01

PB - American Chemical Society (ACS)

SP - 3440-3448

IS - 11

VL - 62

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{1997_Beaulieu,

author = {Pierre L Beaulieu and Pierre Lavallée and Abraham and Paul C. Anderson and Colette Boucher and YVES BOUSQUET and Jean-Simon Duceppe and James Gillard and Vida Gorys and Chantal Grand-Maître and Louis Grenier and Yvan Guindon and Ingrid Guse and Louis Plamondon and François Soucy and Serge Valois and Dominik Wernic and Christiane Yoakim},

title = {Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor},

journal = {Journal of Organic Chemistry},

year = {1997},

volume = {62},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/jo9702655},

number = {11},

pages = {3440--3448},

doi = {10.1021/jo9702655}

}

MLA

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MLA Copy

Beaulieu, Pierre L., et al. “Practical, Stereoselective Synthesis of Palinavir, a Potent HIV Protease Inhibitor.” Journal of Organic Chemistry, vol. 62, no. 11, May. 1997, pp. 3440-3448. https://doi.org/10.1021/jo9702655.

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Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

SJR

0.724

CiteScore

6.2

Impact factor

3.3

ISSN

00223263 (Print)

15206904 (Electronic)