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10-Deacetoxy-paclitaxel is a derivative of paclitaxel where the acetoxy group at the C10 position is removed. It can be synthesized through electrochemical reduction of paclitaxel or via samarium diiodide-mediated deoxygenation. Additionally, it serves as a precursor for further chemical modifications, such as epoxidation, to form novel pentacyclic structures. Deuterated versions, like 10-deacetoxy-(10α-2H)paclitaxel, can also be prepared for research purposes.

148121-24-8

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148121-24-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 148121-24-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,8,1,2 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 148121-24:
(8*1)+(7*4)+(6*8)+(5*1)+(4*2)+(3*1)+(2*2)+(1*4)=108
108 % 10 = 8
So 148121-24-8 is a valid CAS Registry Number.

148121-24-8Relevant academic research and scientific papers

Electrochemical Reduction of Taxoids: Selective Preparation of 9-dihydro-, 10-deoxy- and 10-deacetoxy-Taxoids

Pulicani, Jean-Pierre,Bourzat, Jean-Dominique,Bouchard, Herve,Commercon, Alain

, p. 4999 - 5002 (1994)

The electrochemical reduction of docetaxel in methanol in the presence of ammonium chloride leads to 9α-dihydro-docetaxel 3 and 9β-dihydro-docetaxel 4.Under the same conditions, the electrochemical reduction of paclitaxel gives 10-deacetoxy-paclitaxel 7.C

The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-expoxypaclitaxel

Harriman,Jalluri,Grunewald,Vander Velde,Georg,Himes

, p. 8909 - 8912 (1995)

Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to pla

A one-step synthesis of a deuterated paclitaxel analogue: 10-deacetoxy- (10α-2H)paclitaxel

Dutta, Dinah,Hadd, Harry,Vander Velde, David G.,Georg, Gunda I.

, p. 3277 - 3278 (1999)

10-Deacetoxy-(10α-2H)paclitaxel was prepared in one step via the samarium diiodide mediated deoxygenation of paclitaxel in the presence of D2O.

METHOD FOR SEPARATION AND PURIFICATION OF 13-DEHYDROXYBACCATIN III AND 10-DEACETYLPACLITAXEL FROM TAXANS-CONTAINING MATERIALS

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Page/Page column 6, (2008/06/13)

This invention is directed to a method for efficiently separating and purifying 13-dehydroxybaccatin III and 10-deacetylpaclitaxel with a high purity of 90% or higher purity, preferably 99.5% or higher purity, from taxane-containing materials such as Taxus species, and the thusly obtained highly pure 13-dehydroxybaccatin III and 10-deacetylpaclitaxel can be used as semi-synthetic precursors of paclitaxel and/or docetaxel that are anticancer agents.

Synthesis and interactions of 7-deoxy-, 10-deacetoxy, and 10-deacetoxy-7-deoxypaclitaxel with NCI/ADR-RES cancer cells and bovine brain microvessel endothelial cells

Ge, Haibo,Vasandani, Veena,Huff, Jacquelyn K.,Audus, Kenneth L.,Himes, Richard H.,Seelig, Anna,Georg, Gunda I.

, p. 433 - 436 (2007/10/03)

7-Deoxypaclitaxel, 10-deacetoxypaclitaxel and 10-deacetoxy-7- deoxypaclitaxel were prepared and evaluated for their ability to promote assembly of tubulin into microtubules, their cytotoxicity against NCI/ADR-RES cells and for their interactions with P-gl

Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups

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Page column 54, (2010/02/06)

Process for the preparation of a derivative or analog of baccatin III or 10-desacetyl baccatin III having a C2 substituent other than benzoate and/or a C4 substituent other than acetate in which the C2 benzoate substituent and/or the C4 acetate substituen

Synthesis of a novel C-10 spiro-epoxide of paclitaxel

Walker, Michael A.,Johnson, Timothy D.,Huang, Stella,Vyas, Dolatorai M.,Kadow, John F.

, p. 1683 - 1685 (2007/10/03)

New analogues of paclitaxel (1a, active constituent of Taxol) were synthesized containing an epoxide at the C-10 position. The introduction of the epoxide was carried out by selective removal of the C10-acetate followed by protection of the C2′- and C7-hydroxyl groups. After oxidation to yield a ketone at the C10-position, this intermediate was reacted with dimethylsulfonium ylide. Deprotection and further manipulations provide the C10-spiro epoxide of paclitaxel (1b) and the corresponding C7-MOM ether (1c).

Process for the preparation of 10-desacetoxybaccatin III

-

, (2008/06/13)

A process for abstracting a C10 hydroxy, acyloxy or sulfonyloxy substituent from a taxane in which the C10 hydroxy, acyloxy or sulfonyloxy substituted taxane is reacted with samarium diiodide.

10-desacetoxytaxol derivatives

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, (2008/06/13)

The present invention relates to 10-desacetoxytaxol and derivatives thereof, which are useful as antitumor agents. These compounds have the formula STR1 wherein R2 is hydrogen, hydroxy or a protected hydroxy group; R3 and R4 are independently hydrogen, hydroxy, a protected hydroxy group, methyl, --SH, --NH2, or --NR8 R9 ; R5 is R10, or --OR10 ; R6 and R7 are independently hydrogen, alkyl, or aryl; R8 and R9 are independently hydrogen, alkyl, alkenyl, alkynyl, or aryl; and R10 is alkoxy, alkyl, alkenyl, alkynl, or aryl.

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