851856-99-0

Basic information

• Product Name: 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester
• Synonyms: 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS NO: 851856-99-0
• Molecular Weight: 586.847
• Mol File: 851856-99-0.mol

Chemical Properties

• CAS DataBase Reference: 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester(851856-99-0)
• EPA Substance Registry System: 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester(851856-99-0)

Safety Data

• Hazardous Substances Data: 851856-99-0(Hazardous Substances Data)

Upstream product

• 851856-98-9 5-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 7677-24-9 trimethylsilyl cyanide 
• 73286-71-2 N-(tert-butoxycarbonyl)-2,3-dihydropyrrole 
• 134409-06-6 4,4-ethylenedioxy-2,2-dimethylcyclohexanone 
• 851857-08-4 tert-butyl-(9,9-dimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-yloxy)-diphenyl-silane 
• 851856-96-7 4-(tert-butyl-diphenyl-silanyloxy)-5,5-dimethyl-cyclohex-2-enone 
• 851856-97-8 5-(propane-2-sulfonyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 851857-14-2 N-(tert-butoxycarbonyl)-2-hydroxymethyl-4,5-dihydropyrrole 
• 851856-95-6 (R)-9,9-Dimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-ol 
• 851857-00-6 9,9-dimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one 

Downstream Products

• 960307-29-3 C₂₇H₂₅N₃O₃ 
• 960307-44-2 C₂₇H₂₅N₃O₅ 
• 960307-28-2 C₂₉H₂₅N₃O₃ 
• 960307-42-0 C₂₉H₂₅N₃O₅ 
• 960307-26-0 C₂₇H₂₅N₃O₃ 
• 960307-41-9 C₂₇H₂₅N₃O₅ 
• 960307-25-9 C₂₇H₂₅N₃O₃ 
• 960307-40-8 C₂₇H₂₅N₃O₅ 
• 851857-02-8 (2R,4'aR,6'S,7'S,8'aS)-6'-(tert-Butyl-diphenyl-silanyloxy)-8'a-hydroxy-5',5'-dimethyl-2'-oxo-7'-phenylsulfanyl-octahydro-spiro[pyrrolidine-2,3'-quinoline]-1-carboxylic acid tert-butyl ester 
• 851857-03-9 (2R,4'aR,6'S,7'S)-6'-(tert-Butyl-diphenyl-silanyloxy)-5',5'-dimethyl-1-(1-methyl-cyclohexa-2,5-dienecarbonyl)-7'-phenylsulfanyl-1',4',4'a,5',6',7'-hexahydro-spiro[pyrrolidine-2,3'-quinolin]-2'-one 
• 851857-01-7 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-carbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 851857-11-9 (2R,4'aR,6'S,7'S)-6'-(tert-Butyl-diphenyl-silanyloxy)-5',5'-dimethyl-7'-phenylsulfanyl-1',4',4'a,5',6',7'-hexahydro-spiro[pyrrolidine-2,3'-quinolin]-2'-one 
• 851857-04-0 C₃₁H₃₈N₂O₃Si 
• 851857-10-8 2-[5-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-2-oxo-cyclohex-3-enylmethyl]-2-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

TARGETING THE ONCOPROTEIN NUCLEOPHOSMIN

(+)-Avrainvillamide, a naturally occurring alkaloid with antiproliferative activity, is shown to bind to the oncoprotein nucleophosmin. Nucleophosmin is known to regulate the tumor suppressor protein p53 and is overexpressed in many different human tumors. The invention provides methods of modulating nucleophosmin and p53 using (+)-avrainvillamide and analogues thereof. These compounds may provide leads for the development of novel anti-cancer therapies that target nucleophosmin.

SYNTHESIS OF AVRAINVILLAMIDE, STEPHACIDIN B, AND ANALOGUES THEREOF

The syntheses of the natural products, avrainvillamide and stephacidin B, are provided. The α,β-unsaturated nitrone functionality of avrainvillamide and its 3- alkylidene-3H-indole 1 -oxide core is shown to covalently and reversibly bond to heteroatom-based nucleophiles. This capability may allow these molecules to bind active site nucleophiles and may provide the basis for designing potent and selective enayme inhibitors. Both avrainvillamide and its dimer stephacidin B have been reported to exhibit antiproliferative activity, and avrainvillamide has been reported to exhibit antimicrobial activity against multi-drug resistant bacteria. Avrainvillamide has been found to target cytoskeleton-linking membrane protein (CLIMP-63) thereby preventing cells from undergoing mitosis. The invention provides syntheses of these natural products as well as analogs of these natural products and their functional cores. The compounds of the invention may be used in the treatment of diseases such as cancer, autoimmune diseases, and bacterial infection.

Enantioselective synthesis of stephacidin B

We describe an enantioselective synthetic route to the antiproliferative alkaloid stephacidin B (1) proceeding in 18 steps and 4.0% yield from 4,4-(ethylenedioxy)-2,2-dimethylcyclohexanone (3). Key features of the synthetic sequence include the use of the Corey-Bakshi-Shibata (CBS) reduction to introduce asymmetry early in the synthetic route, use of the novel electrophile N-(tert-butoxycarbonyl)-5-(isopropylsulfonyloxymethyl)-2,3-dihydropyrrole in a stereoselective enolate alkylation, a diastereoselective Strecker-type addition of hydrogen cyanide to an N-Boc enamine substrate in the solvent hexafluoroisopropanol, platinum-catalyzed nitrile hydrolysis under neutral conditions, cyclization of an acylamino radical intermediate to form the diketopiperazine core of stephacidin B, and implementation of a convergent procedure for introduction of the key 3-alkylidene-3H-indole 1-oxide functional group in the final stage of the route to prepare the structure 2, previously proposed to be the fungal metabolite avrainvillamide (17 steps, 4.2% yield). We observed that synthetic (-)-2 dimerized in the presence of triethylamine to form (+)-stephacidin B (>95%). We also obtained evidence that 2 can form 1 under mild conditions, and that 2 reacts with nucleophiles, such as methanol, by conjugate addition. Copyright