19605-80-2

Basic information

• Product Name: taxusin
• Synonyms: taxusin;(1R)-5α,9α,10β,13α-Tetraacetoxy-taxa-4(20),11-diene;5α,9α,10β,13α-Tetraacetoxytaxa-4(20),11-diene;Taxa-4(20),11-diene-5α,9α,10β,13α-tetrol 5,9,10,13-tetraacetate;Taxa-4(20),11-diene-5α,9α,10β,13α-tetrol tetraacetate;TAXUSIN(P)
• CAS NO: 19605-80-2
• Molecular Formula: C28H40O8
• Molecular Weight: 504.616
• Mol File: 19605-80-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 131～132℃
• Boiling Point: 537.3°Cat760mmHg
• Flash Point: 224.4°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.29E-11mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: taxusin(CAS DataBase Reference)
• NIST Chemistry Reference: taxusin(19605-80-2)
• EPA Substance Registry System: taxusin(19605-80-2)

Safety Data

• Hazardous Substances Data: 19605-80-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A taxane diterpenoid that is taxa-4(20),11-diene in which the 5alpha, 9alpha, 10beta and 13alpha hydrogens have been replaced by acetoxy groups. It is a prominent secondary metabolite of y w heartwood.

InChI:InChI=1/C28H40O8/c1-14-21-12-20-13-23(34-17(4)30)15(2)24(27(20,7)8)25(35-18(5)31)26(36-19(6)32)28(21,9)11-10-22(14)33-16(3)29/h20-23,25-26H,1,10-13H2,2-9H3/t20-,21-,22+,23+,25-,26+,28-/m1/s1

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 226938-56-3 Acetic acid (1R,3S,5S,8R,9R,10R,13S)-5,9,13-triacetoxy-8,12,15,15-tetramethyl-4-oxo-tricyclo[9.3.1.0^3,8]pentadec-11-en-10-yl ester 
• 226910-55-0 (R)-1-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-2-enol 
• 226910-59-4 2,2-Dimethyl-propionic acid (R)-2-{(R)-5-[1-benzyloxy-meth-(Z)-ylidene]-4,6,6-trimethyl-3-triisopropylsilanyloxy-cyclohex-3-enylmethyl}-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester 
• 226910-70-9 Trifluoro-methanesulfonic acid (1R,3S,8R,9R,10R,13S)-10,13-bis-(tert-butyl-dimethyl-silanyloxy)-8,12,15,15-tetramethyl-9-trimethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-4,11-dien-4-yl ester 
• 226910-64-1 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester 
• 226910-56-1 (R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone 
• 226910-71-0 (1R,3S,8R,9R,10R,13S)-10,13-Bis-(tert-butyl-dimethyl-silanyloxy)-8,12,15,15-tetramethyl-4-trimethylsilanylmethyl-9-trimethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-4,11-diene 
• 226910-66-3 C₃₉H₅₄O₄Si 
• 226910-79-8 C₃₉H₅₆O₄Si 
• 226910-72-1 (1R,3R,5S,8R,9R,10R,13S)-10,13-Bis-(tert-butyl-dimethyl-silanyloxy)-8,12,15,15-tetramethyl-4-methylene-9-trimethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-5-ol 
• 226910-58-3 2,2-Dimethyl-propionic acid (R)-2-((R)-3-benzyloxymethyl-2,2,4-trimethyl-5-oxo-cyclohex-3-enylmethyl)-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester 
• 226910-65-2 (1R,4R,9R,10R,13S)-9,10-Bis-benzyloxy-12,15,15-trimethyl-13-triethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-ol 
• 226910-69-6 (1R,3S,8R,9R,10R,13S)-10,13-Bis-(tert-butyl-dimethyl-silanyloxy)-8,12,15,15-tetramethyl-9-trimethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-one 

Related news

Stereoselective synthesis of an advanced taxusin (cas 19605-80-2) intermediate: an application of the type 2 intramolecular Diels–Alder reaction☆08/25/2019

Stereoselective synthesis of an advanced taxusin intermediate is described. The key step is the successful application of the type 2 intramolecular Diels–Alder (IMDA) reaction for the assembly of the tricyclic core of this natural product.detailed

Relevant articles and documents

Enantioselective total synthesis of (+)-taxusin

For the total synthesis of (+)-taxusin, the AC-ring fragment 8 was prepared from an optically active 2-bromo-3-siloxycyclohexenecarbacetal 5 via 4 steps and was converted to the dienol silyl ether 13. The thus-obtained 13 underwent B-ring cyclization in the presence of Me2AlOTf to produce the ABC endo-tricarbocycle 14 having C9α, C10β-substituents, which was converted to the cyclopropyl ketone 21a. Introduction of C19 methyl via reductive cleavage of the cyclopropane ring under Birch conditions and successive in situ treatment of the resulting enol with methanol gave the C3α-protonated ketone 24. Next, 24 was converted to the allylsilane 29, which was then oxidized with m-CPBA to produce the fully functionalized taxusin carbon skeleton. Finally, removal of the silyl protecting groups followed by acetylation completed the total synthesis of (+)-taxusin.