13452-36-3

Basic information

• Product Name: (7R,12S,15S)-O~15~-acetyl-7,8-bis(acetyloxy)-2-hydroxy-4-oxo-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-13,20-didehydro-7,8,9,10,11,12,13,14-octahydro-2,15:9,14-dicycloretinol
• Synonyms: 13452-36-3; O-Cinnamoyltaxicin-I triacetate
• CAS NO: 13452-36-3
• Molecular Formula: C₃₅H₄₂O₁₀
• Molecular Weight: 622.702
• Mol File: 13452-36-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 690.2°C at 760 mmHg
• Flash Point: 209.8°C
• Density: 1.25g/cm³
• Vapor Pressure: 5.31E-20mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: (7R,12S,15S)-O~15~-acetyl-7,8-bis(acetyloxy)-2-hydroxy-4-oxo-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-13,20-didehydro-7,8,9,10,11,12,13,14-octahydro-2,15:9,14-dicycloretinol(CAS DataBase Reference)
• NIST Chemistry Reference: (7R,12S,15S)-O~15~-acetyl-7,8-bis(acetyloxy)-2-hydroxy-4-oxo-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-13,20-didehydro-7,8,9,10,11,12,13,14-octahydro-2,15:9,14-dicycloretinol(13452-36-3)
• EPA Substance Registry System: (7R,12S,15S)-O~15~-acetyl-7,8-bis(acetyloxy)-2-hydroxy-4-oxo-12-{[(2Z)-3-phenylprop-2-enoyl]oxy}-13,20-didehydro-7,8,9,10,11,12,13,14-octahydro-2,15:9,14-dicycloretinol(13452-36-3)

Safety Data

• Hazardous Substances Data: 13452-36-3(Hazardous Substances Data)

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 146278-52-6 Triacetylphototaxicin I 
• 273926-80-0 C₅₂H₆₆N₅O₁₅PSi 
• 273926-79-7 C₅₂H₆₄N₅O₁₅PSi 
• 273926-78-6 C₄₆H₅₀N₅O₁₅P 
• 273926-84-4 C₅₂H₅₃NO₁₃ 
• 273926-83-3 C₃₆H₄₀O₁₀ 
• 273926-82-2 C₃₆H₃₈O₁₀ 
• 273926-75-3 C₃₆H₄₀O₁₀ 
• 273926-45-7 C₃₀H₃₄O₈ 
• 266676-47-5 C₆₆H₆₉NO₁₇ 
• 266676-48-6 C₅₉H₆₃NO₁₇ 
• 266676-52-2 C₄₅H₅₅N₅O₁₆ 
• 266676-43-1 C₄₅H₅₃N₅O₁₆ 
• 266676-46-4 C₄₂H₅₀O₁₃ 

Relevant articles and documents

Total Synthesis of 1-Hydroxytaxinine

1-Hydroxytaxinine (1) is a cytotoxic taxane diterpenoid. Its central eight-membered B-ring possesses four oxygen-functionalized centers (C1, C2, C9, and C10) and two quaternary carbon centers (C8 and C15), and is fused with six-membered A- and C-rings. The densely functionalized and intricately fused structure of 1 makes it a highly challenging synthetic target. Reported here is an efficient radical-based strategy for assembling 1 from A- and C-ring fragments. The A-ring bearing an α-alkoxyacyl telluride moiety underwent intermolecular coupling with the C-ring fragment by a Et3B/O2-promoted decarbonylative radical formation. After construction of the C8-quaternary stereocenter, a pinacol coupling reaction using a low-valent titanium reagent formed the B-ring with stereoselective installation of the C1,C2-diol. Subsequent manipulations at the A- and C-rings furnished 1 in 26 total steps.