4297-61-4

Usage

InChI:InChI=1/C21H28O8/c1-11-6-7-20(9-25-12(2)22)15(8-11)29-18-16(27-13(3)23)17(28-14(4)24)19(20,5)21(18)10-26-21/h8,15-18H,6-7,9-10H2,1-5H3/t15?,16-,17?,18-,19-,20?,21+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 111488-05-2 3α,4β-diacetoxy-10β-bromo-9α,15;12,13-epi-diepoxytrichothecane 
• 2270-40-8 4,15-diacetoxyscirpenol 
• 557-34-6 zinc diacetate 
• 6121-60-4 3,15-diacetoxyscirpenol 
• 85925-84-4 Acetic acid (6R,7S,8S,9S)-7-acetoxy-9-((R)-1-acetoxymethyl-4-hydroxy-4-methyl-cyclohex-2-enyl)-8-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,4-dioxa-spiro[4.4]non-6-yl ester 
• 85925-74-2 C₂₈H₄₀O₈Si 
• 85925-76-4 C₂₉H₄₂O₇Si 
• 85925-75-3 C₂₈H₃₈O₇Si 
• 85925-79-7 C₂₆H₄₂O₈Si 
• 85925-72-0 C₂₆H₃₉NO₆Si 
• 85925-73-1 C₂₄H₃₄O₇Si 
• 85925-85-5 Acetic acid (R)-1-[(6S,7S,8S,9R)-7-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-6-methyl-1,4-dioxa-spiro[4.4]non-6-yl]-4-hydroxy-4-methyl-cyclohex-2-enylmethyl ester 
• 85925-86-6 C₂₄H₄₀O₇Si 

Relevant academic research and scientific papers

Chemical Deoxygenation of the Trichothecenes, Diacetoxyscirpenol and Deoxynivalenol

Based on a model study using the bicyclic epoxides (9) and (10), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene toxins has been devised.

Chemical Deoxygenation of the Trichothecenes Diacetoxyscirpenol and Deoxynivalenol

Based on a model study using the bicyclooctane epoxy acetates (14) and (15), an efficient one-step procedure for the selective removal of the 12,13-epoxide ring of the trichothecene mycotoxins diacetoxyscirpenol (1; R=H) and deoxynivalenol (2; R=H) has been devised.The key to success proved to be use of the lower-valent tungsten deoxygenation system of Sharpless et al.

Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene

The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.

Synthesis and Biological Evaluation of a Trichothecene epi-Epoxide, 3α,4β,15-Triacetoxy-12,13-epi-epoxytrichothec-9-ene

In order to provide additional insight into the mode of action of the trichothecene mycotoxins, one of the first semi-synthetic trichothecene epi-epoxides (8) has been prepared; in dramatic contrast to its natural isomer (9), this compound proved tobe devoid of significant biological activity.