Synthesis of novel thiol surrogate of Taxol®: 2′-deoxy-2′- mercaptopaclitaxel

Xin Qi; Sang Hyeup Lee; Juyoung Yoon; Yoon Sik Lee

doi:10.1016/j.tet.2004.02.047

Synthesis of novel thiol surrogate of Taxol®: 2′-deoxy-2′- mercaptopaclitaxel

Xin Qi, Sang Hyeup Lee, Juyoung Yoon, Yoon Sik Lee

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of Taxol^® by coupling (4S, 5S)-2,4-diphenyloxazoline-5-carboxylic acid with 7-triethylsilyl baccatin III, followed by ring-opening of the oxazoline intermediate with thiolacetic acid is described.

Original language	English
Pages (from-to)	3599-3603
Number of pages	5
Journal	Tetrahedron
Volume	60
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2004.02.047
State	Published - 12 Apr 2004

Bibliographical note

Funding Information:
We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.

Keywords

Mercaptopaclitaxel
Oxazoline
Taxol

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10.1016/j.tet.2004.02.047

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title = "Synthesis of novel thiol surrogate of Taxol{\textregistered}: 2′-deoxy-2′- mercaptopaclitaxel",

abstract = "Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of Taxol{\textregistered} by coupling (4S, 5S)-2,4-diphenyloxazoline-5-carboxylic acid with 7-triethylsilyl baccatin III, followed by ring-opening of the oxazoline intermediate with thiolacetic acid is described.",

keywords = "Mercaptopaclitaxel, Oxazoline, Taxol",

author = "Xin Qi and Lee, {Sang Hyeup} and Juyoung Yoon and Lee, {Yoon Sik}",

note = "Funding Information: We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.",

year = "2004",

month = apr,

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doi = "10.1016/j.tet.2004.02.047",

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T1 - Synthesis of novel thiol surrogate of Taxol®

T2 - 2′-deoxy-2′- mercaptopaclitaxel

AU - Qi, Xin

AU - Lee, Sang Hyeup

AU - Yoon, Juyoung

AU - Lee, Yoon Sik

N1 - Funding Information: We thank Hanmi Pharmaceutical Co., Ltd for the generous donation of 10-deacetylbaccatin III. This work was supported by Korea Science and Engineering Foundation (R14-2003-014-01001-0) and the Brain Korea 21 Program.

PY - 2004/4/12

Y1 - 2004/4/12

N2 - Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of Taxol® by coupling (4S, 5S)-2,4-diphenyloxazoline-5-carboxylic acid with 7-triethylsilyl baccatin III, followed by ring-opening of the oxazoline intermediate with thiolacetic acid is described.

AB - Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of Taxol® by coupling (4S, 5S)-2,4-diphenyloxazoline-5-carboxylic acid with 7-triethylsilyl baccatin III, followed by ring-opening of the oxazoline intermediate with thiolacetic acid is described.

KW - Mercaptopaclitaxel

KW - Oxazoline

KW - Taxol

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U2 - 10.1016/j.tet.2004.02.047

DO - 10.1016/j.tet.2004.02.047

M3 - Article

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SN - 0040-4020

VL - 60

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EP - 3603

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

Synthesis of novel thiol surrogate of Taxol®: 2′-deoxy-2′- mercaptopaclitaxel

Abstract

Bibliographical note

Keywords

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