226910-59-4

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 226910-59-4
• Molecular Weight: 835.252
• Mol File: 226910-59-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(226910-59-4)
• EPA Substance Registry System: 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(226910-59-4)

Safety Data

• Hazardous Substances Data: 226910-59-4(Hazardous Substances Data)

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 226910-57-2 (R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-hydroxy-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone 
• 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 
• 226910-56-1 (R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone 
• 226910-55-0 (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 

Downstream Products

• 116002-25-6 taxusin 
• 226910-73-2 C₃₃H₄₀O₄ 
• 226910-60-7 2,2-Dimethyl-propionic acid (1R,4R,9R,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester 
• 226910-63-0 2,2-Dimethyl-propionic acid (1R,4R,9R,10R,13S)-9,10-bis-benzyloxy-13-hydroxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl 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 
• 226910-79-8 C₃₉H₅₆O₄Si 
• 226910-66-3 C₃₉H₅₄O₄Si 
• 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 
• 226910-62-9 2,2-Dimethyl-propionic acid (1R,4R,9S,10R)-9,10-bis-benzyloxy-12,15,15-trimethyl-13-oxo-tricyclo[9.3.1.0^3,8]pentadeca-3⁽⁸⁾,11-dien-4-yl ester 

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.