Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Base Information

Chemical Name:Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester
CAS No.:455252-83-2
Molecular Formula:C₂₂H₃₄O₂S₂
Molecular Weight:394.643
Hs Code.:

Synonyms:Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

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Chemical Property of Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

There total 12 articles about Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester 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:

: Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester

: 74-88-4
methyl iodide

: 455252-83-2
Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 70 ℃;
DOI:10.1016/S0040-4039(02)00729-3

Reference yield:

: 80-57-9,1196-01-6
(-)-Verbenone

: 455252-83-2
Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 85 percent / CuI

2.1: LiAlH₄ / tetrahydrofuran / -78 °C

3.1: imidazole / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 60 percent / Me₂S

5.1: 56 percent / Dess-Martin periodinane

6.1: 93 percent / n-BuLi / tetrahydrofuran / -78 °C

7.1: O₃; Me₂S / CH₂Cl₂ / -78 °C

7.2: KOH / methanol

8.1: 90 percent / p-toluenesiulfonic acid / methanol / 3 h / 25 °C

9.1: NaH; HMPA / tetrahydrofuran

10.1: HMPA / tetrahydrofuran / 70 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00729-3

Reference yield:

: 55314-73-3
(S)-citronellyl magnesium bromide

: 455252-83-2
Dithiocarbonic acid O-{(1S,2S,4S,5S)-4-[2-((S)-1,3-dimethyl-4-oxo-cyclohex-2-enyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 85 percent / CuI

2.1: LiAlH₄ / tetrahydrofuran / -78 °C

3.1: imidazole / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 60 percent / Me₂S

5.1: 56 percent / Dess-Martin periodinane

6.1: 93 percent / n-BuLi / tetrahydrofuran / -78 °C

7.1: O₃; Me₂S / CH₂Cl₂ / -78 °C

7.2: KOH / methanol

8.1: 90 percent / p-toluenesiulfonic acid / methanol / 3 h / 25 °C

9.1: NaH; HMPA / tetrahydrofuran

10.1: HMPA / tetrahydrofuran / 70 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00729-3