158830-49-0

Basic information

• Product Name: Δ^6,7-paclitaxel
• Synonyms: Δ^6,7-paclitaxel
• CAS NO: 158830-49-0
• Molecular Weight: 835.905
• Mol File: 158830-49-0.mol

Chemical Properties

• CAS DataBase Reference: Δ^6,7-paclitaxel(CAS DataBase Reference)
• NIST Chemistry Reference: Δ^6,7-paclitaxel(158830-49-0)
• EPA Substance Registry System: Δ^6,7-paclitaxel(158830-49-0)

Safety Data

• Hazardous Substances Data: 158830-49-0(Hazardous Substances Data)

Upstream product

• 165065-02-1 2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel 
• 165065-01-0 2'-O-(t-butyldimethylsilyl)-7β-O-trifluoromethanesulfonyl-paclitaxel 
• 114655-02-6 2'-O-(tert-butyldimethylsilyl)paclitaxel 
• 211572-24-6 C₅₃H₆₃NO₁₄Si 
• 171780-95-3 2'-O-acetyl-Δ^6,7-paclitaxel 
• 33069-62-4 taxol 
• 148930-54-5 (2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 
• 171781-02-5 C₄₈H₅₀F₃NO₁₆S 
• 171780-98-6 2'-O-acetyl-7-trifluoromethanesulfonyl-paclitaxel 
• 171869-48-0 2'-O-acetyl-7α-methanesulfonyl-paclitaxel 
• 92950-40-8 2'-O-acetyl-paclitaxel 
• 172586-62-8 2'-O-acetyl-7α-paclitaxel 

Downstream Products

• 153212-75-0 6-α-hydroxy-7-α-paclitaxel 
• 171780-96-4 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-Δ^6,7-20-O-seco-paclitaxel 

Relevant articles and documents

Crystallographic determination of the stereochemistry of C-6,7 epoxy paclitaxel

The Stereochemistry of C-6,7 epoxy paclitaxel was determined by single crystal X-ray analysis of the baccatin derivative to be 6α, 7α. This finding corrects the structure reported by Kingston et al based on NOE data and corrects the discrepancy reported f

Paclitaxel analogs modified in ring C: Synthesis and biological evaluation

Lead tetracetate oxidation of 6α-hydroxy-7-epi-paclitaxel lends to C-nor-paclitaxel and C-seco-paclitaxel derivatives. Tetrpropylammonium perruthnate (TPAP) oxidation of a 6α-hydroxy-7-epi-paclitaxel derivative leads to a 6-formyl-C-nor-paclitaxel derivative. Reaction of a 6α-O-trifluoromethanesulfonyl-7-epi-paclitaxel derivative with DMAP yields a 20-O-acetyl-4-deacetyl-5,6-dehydro-6-formyl-C-nor-paclitaxel derivative. C-nor-paclitaxel analogs are less active than paclitaxel.

Synthesis of novel taxol analogs and evaluation of their biological activities

Two new taxol analogs 6 and 10 have been prepared from baccatin III (1) and taxol (7a), respectively. Like taxol, both compounds were found to promote microtubule formation and stabilization, although they were less active than taxol. Both 6 and 10 exhibi

Synthesis and Molecular Modeling of Taxanes Modified at Ring C

Some new paclitaxel analogs, modified at ring C, - namely the 7-α-mesylate, 7-deoxy-7-α-amino, 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-Δ6,7-20-O-seco and 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-6,7-epoxy-20-O-seco derivatives - are presented. The biological activity of 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-Δ6,7-20-O-seco, 4-deacetoxy-4α-hydroxy-4β-hydroxymethyl-5α-acetoxy-6,7-epoxy-20-O-seco, 7-deoxy-7-α-azido, 7-deoxy-7-α-amino and 6,7-epoxy derivatives heve been evaluated. A molecular modeling study on some paclitaxel derivatives has been done in an attempt to rationalize the difference in biological activity.

Synthesis and Biological Evaluation of Paclitaxel Analogs Modified in Ring C

Both 7-deoxy-7α-azidopaclitaxel (6) and 7-deoxy-Δ6,7-paclitaxel (4) can be prepared from paclitaxel-7-O-triflate (2b).Oxidation of 7-deoxy-Δ6,7-paclitaxel with dioxirane yields the epoxide 7, while oxidation with osmium tetroxide yie