92950-40-8

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Uses

2''-Acetyltaxol is a microtubule polymerization-inactive taxol analog.

InChI:InChI=1/C49H53NO15/c1-26-33(63-45(58)39(62-28(3)52)37(30-17-11-8-12-18-30)50-43(56)31-19-13-9-14-20-31)24-49(59)42(64-44(57)32-21-15-10-16-22-32)40-47(7,34(54)23-35-48(40,25-60-35)65-29(4)53)41(55)38(61-27(2)51)36(26)46(49,5)6/h8-22,33-35,37-40,42,54,59H,23-25H2,1-7H3,(H,50,56)/t33-,34-,35+,37-,38+,39+,40-,42-,47+,48-,49+/m0/s1

Upstream product

• 33069-62-4 taxol 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 90332-63-1 7-O-(β-xylosyl)-10-deacetyltaxol 
• 78432-77-6 10-deacetylpaclitaxel 
• 108-05-4 vinyl acetate 

Downstream Products

• 33069-62-4 taxol 
• 171780-95-3 2'-O-acetyl-Δ^6,7-paclitaxel 
• 171780-96-4 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-Δ^6,7-20-O-seco-paclitaxel 
• 158830-49-0 Δ^6,7-paclitaxel 
• 171780-98-6 2'-O-acetyl-7-trifluoromethanesulfonyl-paclitaxel 
• 100431-63-8 2'-acetyl-7-oxo-5,O-secotaxol 
• 100431-60-5 2'-acetyl-7-oxo-5,6-dehydro-5,O-secotaxol 
• 100431-54-7 2'-acetyl-7-oxotaxol 

Relevant academic research and scientific papers

Process of synthesizing paclitaxel from 10-deacetyltaxol

The invention relates to a process of synthesizing paclitaxel from 10-deacetyltaxol (10-DAT). The process includes: taking 10-DAT as the starting raw material, conducting acetic anhydride acetylation,and under an alkaline condition, hydrolyzing the 2'-acetyl with dimethylamine to obtain paclitaxel. The route has the characteristics of short steps, shortened production cycle, no need for side chain, and reduction of the raw material cost.

Effect of XlogP and Hansen Solubility Parameters on Small Molecule Modified Paclitaxel Anticancer Drug Conjugates Self-Assembled into Nanoparticles

Small molecule modified anticancer drug conjugates (SMMDCs) can self-assemble into nanoparticles (NPs) as therapeutic NP platforms for cancer treatment. Here we demonstrate that the XlogP and Hansen solubility parameters of paclitaxel (PTX) SMMDCs is essential for SMMDCs self-assembling into NPs. The amorphous state of PTX SMMDCs will also affect SMMDCs self-assembling into NPs. However, the antitumor activity of these PTX SMMDCs NPs decreased along with their XlogP values, indicating that a suitable XlogP value for designing the SMMDCs is important for self-assembling into NPs and for possessing antitumor activity. For higher level XlogP SMMDCs, a degradable linker should be considered in the design of SMMDCs to overcome the problem of lower antitumor activity. It is preferable that the hydrophilic groups in the SMMDCs should be present on the surface of self-assembling NPs.

METHOD FOR THE PREPARATION OF SYNTHESIZED TAXANOIDS

The present invention relates to a process for the preparation of synthetic taxanes, which protects C(7)-OH with lanthanon compounds. Its advantages are simple process and firm & reliable binding. Moreover, no C(7)-acylated taxanes are produced in the subsequent steps, and hydrolysis of C(2')-ester groups in acylated products becomes readily controllable. In the process for the preparation of synthetic taxanes, tetrahydrofuran is used in the present invention as a medium for acylation, which not only achieves the same effects as pyridine, but also avoids odor, so as to solve the problem regarding the extremely high requirements for the place of production. The present invention can be used for the preparation of not only semi-synthetic taxane using natural taxanes as raw material, but also full-synthetic taxane.

Process for the Preparation of Synthetic Taxanes

The present invention relates to a process for the preparation of synthetic taxanes, which protects C(7)-OH with lanthanon compounds. Its advantages are simple process and firm & reliable binding. Moreover, no C(7)-acylated taxanes are produced in the subsequent steps, and hydrolysis of C(2′)-ester groups in acylated products becomes readily controllable. In the process for the preparation of synthetic taxanes, tetrahydrofuran is used in the present invention as a medium for acylation, which not only achieves the same effects as pyridine, but also avoids odor, so as to solve the problem regarding the extremely high requirements for the place of production. The present invention can be used for the preparation of not only semi-synthetic taxane using natural taxanes as raw material, but also full-synthetic taxane.

Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates

The first examples of highly water soluble taxol derivatives (0.1 mmol/mL) were prepared by the attachement of polyethylene glycol (molecular weight 2-5 kD) at the 7-position of taxol via a urethane or carbonate linkage.When lower molecular weight polyethylene glycols (350 and 750) were used, the solubilities were considerably lower (1.87E-3 mmol/mL) but still substantially greater than taxol itself.Additional 7-subsituted taxol derivatives were also prepared by utilizing small molecules consisting of sugars and ionic and multifunctional compounds.However, most of these derivatives had solubilities, calculated from HPLC retention times, that did not differ significantly from taxol itself.The use of methoxyacetate as a protecting group during these syntheses is discussed.