N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel

Hari K.R. Santhapuram; Apurba Datta; Oliver E. Hutt; Gunda I. Georg

doi:10.1021/jo800173h

N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel

Hari K.R. Santhapuram
, Apurba Datta
, Oliver E. Hutt
, Gunda I. Georg

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

19 Scopus citations

Abstract

(Chemical Equation Presented) A method has been developed for the methylation of the C3′ amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2′, 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.

Original language	English (US)
Pages (from-to)	4705-4708
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	73
Issue number	12
DOIs	https://doi.org/10.1021/jo800173h
State	Published - Jun 20 2008

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title = "N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel",

abstract = "(Chemical Equation Presented) A method has been developed for the methylation of the C3′ amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2′, 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.",

author = "Santhapuram, \{Hari K.R.\} and Apurba Datta and Hutt, \{Oliver E.\} and Georg, \{Gunda I.\}",

year = "2008",

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T1 - N-methylation of the C3′ amide of taxanes

T2 - Synthesis of N-methyltaxol C and N-methylpaclitaxel

AU - Santhapuram, Hari K.R.

AU - Datta, Apurba

AU - Hutt, Oliver E.

AU - Georg, Gunda I.

PY - 2008/6/20

Y1 - 2008/6/20

N2 - (Chemical Equation Presented) A method has been developed for the methylation of the C3′ amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2′, 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.

AB - (Chemical Equation Presented) A method has been developed for the methylation of the C3′ amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2′, 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.

UR - https://www.scopus.com/pages/publications/45249107046

UR - https://www.scopus.com/pages/publications/45249107046#tab=citedBy

U2 - 10.1021/jo800173h

DO - 10.1021/jo800173h

M3 - Article

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AN - SCOPUS:45249107046

SN - 0022-3263

VL - 73

SP - 4705

EP - 4708

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

N-methylation of the C3′ amide of taxanes: Synthesis of N-methyltaxol C and N-methylpaclitaxel

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