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

Base Information

Chemical Name: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
CAS No.:1366297-73-5
Molecular Formula:C₅₃H₆₄N₂O₆S₃Si₂
Molecular Weight:977.47
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

: 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

: 35572-83-9
α,α-diphenylbenzenemethanesulfenyl chloride

: 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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2012.01.055

Reference yield:

: 1277170-47-4
(6R,8aR)-6-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]tetrahydro-2-methyl-8a-[[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]thio]pyrrolo[1,2-a]pyrazine-1,4,8(8aH)-trione

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate; water / tetrahydrofuran / 0.3 h / 0 °C

2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C

3: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -79 °C

4: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; water; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2012.01.055

Reference yield:

: 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

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C

2: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -79 °C

3: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2012.01.055