148584-49-0

Basic information

• Product Name: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III
• Synonyms: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III
• CAS NO: 148584-49-0
• Molecular Weight: 670.754
• Mol File: 148584-49-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III(CAS DataBase Reference)
• NIST Chemistry Reference: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III(148584-49-0)
• EPA Substance Registry System: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III(148584-49-0)

Safety Data

• Hazardous Substances Data: 148584-49-0(Hazardous Substances Data)

Upstream product

• 142203-65-4 13-acetyl-9-dihydrobaccatin III 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 148584-51-4 7,9-acetonide 13-acetyl-9-dihydrobaccatin III 
• 148584-54-7 9(R)-dihydrotaxol 7,9-acetonide 
• 148584-53-6 9(R)-dihydrotaxol 
• 253335-07-8 C₃₄H₄₂O₁₁ 
• 345983-43-9 13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-triethylsilyloxy-5'-methylhexanoate]-9(R)-dihydro-7,9-isopropylidene-baccatin-III 
• 345983-44-0 13-[(2'R,3'S)-3'-(N-tert-butoxycarbonyl)amino-2'-hydroxy-5'-methylhexanoate]-9(R)-dihydro-baccatin-III 

Relevant articles and documents

Rearrangement of the major taxane from Taxus canadensis

The rearrangement of the major taxane 9-dihydro-13-acetyl-baccatin III (1) to new abeo-taxanes (2,4-6) has been studied. A sequence of reactions has been inferred. Their structures were determined by spectroscopic techniques.

Acid catalyzed rearrangement and acyl migration studies on 9-dihydro- 13-acetylbaccatin-III, a major taxane from Taxus canadensis

A detailed investigation of the rearrangement of the major taxane from Taxus canadensis enables to suggest the sequence of the reactions involved: 9-dihydro-13-acetylbaccatin III - abeo-taxanes with intact oxetane and acyl migration - abeo-taxanes with intact oxetane and deacylation - abeo-taxanes with opening of the oxetane and various acyl migrations including two unusual benzoyl shifts.

An efficient synthesis of the taxane-derived anticancer agent ABT-271

ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a C9-(R)-hydroxyl group as opposed to a C9-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of the C13-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and β-lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.