1277170-47-4

Upstream product

• 1096711-40-8 phenyl [2-[(2R)-2-[[(tert-butyldiphenylsilyl)oxy]methyl]-4-oxopyrrolidin-1-yl]-2-oxoethyl]methylcarbamate 
• 1096711-41-9 (6R)-6-[[(tert-butyldimethylsilyl)oxy]methyl]tetrahydro-2-methylpyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione 
• 1277170-42-9 4-methylbenzenesulfonothioic acid S-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl] ester 
• 119451-80-8 (chloromethoxy)(1,1-dimethylethyl)dimethylsilane 
• 119451-79-5 (1,1-dimethylethyl)[(ethylthio)methoxy]dimethylsilane 

Downstream Products

• 1366297-78-0 (1R,2S,4R,7R)-4-([(tert-butyldiphenylsilyl)oxy]methyl)-2-hydroxy-11-methyl-8,9-dithia-5,11-diazatricyclo[5.2.2.0(1,5)]undecane-6,10-dione 
• 1366297-74-6 (3S,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione 
• 1366297-77-9 (3R,6R,8S,8aR)-3,8a-bis({[(tert-butyldimethylsilyl)oxy]methyl}sulfanyl)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-2-methyl-8-[(triethylsilyl)oxy]octahydropyrrolo[1,2-a]piperazine-1,4-dione 
• 1366297-73-5 ethyl (3R,6R,8S,8aR)-6-([(tert-butyldiphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]-8a-([(triphenylmethyl)sulfanyl]disulfanyl)octahydropyrrolo[1,2-a]piperazine-3-carboxylate 
• 1366297-69-9 ethyl (3R,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate 
• 1366297-71-3 ethyl (3S,6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-2-methyl-1,4-dioxo-8-[(triethylsilyl)oxy]octahydropyrrolo-[1,2-a]piperazine-3-carboxylate 
• 1366297-67-7 (6R,8S,8aR)-6-([(tert-butyldiphenylsilyl)oxy]methyl)-2-methyl-8-[(triethylsilyl)oxy]-8a-([(triphenylmethyl)sulfanyl]disulfanyl)octahydropyrrolo[1,2-a]piperazine-1,4-dione 
• 1366297-64-4 (6R,8S,8aR)-8a-(([(tert-butyldimethylsilyl)oxy]methyl)sulfanyl)-6-([(tert-butyl-diphenylsilyl)oxy]methyl)-8-hydroxy-2-methyloctahydropyrrolo[1,2-a]piperazine-1,4-dione 

Relevant academic research and scientific papers

Synthetic studies related to MPC1001: Formation of a model epidithiodiketopiperazine

A tricyclic epidithiodiketopiperazine was prepared having structural features related to the antitumor antibiotic MPC1001. The method is based on the use of the sulfenylating agent p-MeC6H4S(O 2)SCH2OSiMe2

[[(tert-Butyl)dimethylsilyl]oxy]-methylGroup for sulfur protection

Aromatic and aliphatic thiols can be protected by reaction with t-BuMe 2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH2) 11SCH2OSiMe2Bu-t and three sulfenyl chlorides.