dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Base Information

Chemical Name:dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester
CAS No.:500002-04-0
Molecular Formula:C₂₁H₃₂O₂S₂
Molecular Weight:380.616
Hs Code.:

dithiocarbonic acid <i>O</i>-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester <i>S</i>-methyl ester

Synonyms:dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-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-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-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-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

There total 14 articles about dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-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: 77.0%

: 499797-45-4
dithiocarbonic acid S-methyl ester O-{4,6,6-trimethyl-4-[2-(1-methyl-4-oxo-cyclohexa-2,5-dienyl)-ethyl]-bicyclo[3.1.1]hept-2-yl} ester

: 500002-04-0
dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/ol026820t

Reference yield:

: 499797-48-7
(R)-7-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-5-methyl-heptan-2-ol

: 500002-04-0
dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

4.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

5.1: 19 g / KOH / methanol / 5 h

6.1: LDA; PhSeBr / tetrahydrofuran / 1 h / -78 °C

6.2: m-CPBA / tetrahydrofuran / 1 h

7.1: 2.5 g / TBAF / tetrahydrofuran / 48 h / 50 °C

8.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

8.2: tetrahydrofuran; various solvent(s) / 0.5 h

8.3: 85 percent / HMPA / 24 h

9.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; Phenylselenyl bromide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1021/ol026820t

Reference yield:

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

: 500002-04-0
dithiocarbonic acid O-{4-[2-(4-hydroxy-1-methyl-cyclohexa-2,5-dienyl)-ethyl]-4,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl} ester S-methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: Mg; I₂ / tetrahydrofuran / 0.5 h

1.2: 80 percent / CuI / tetrahydrofuran / -50 - 20 °C

2.1: LiAlH₄ / diethyl ether / 0.25 h

3.1: 4.9 g / imidazole / dimethylformamide / 2.5 h

4.1: O₃ / CH₂Cl₂ / 4 h / -78 °C

5.1: 30.5 g / diethyl ether; tetrahydrofuran / 2 h / 0 °C

6.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

8.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

9.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

10.1: 19 g / KOH / methanol / 5 h

11.1: LDA; PhSeBr / tetrahydrofuran / 1 h / -78 °C

11.2: m-CPBA / tetrahydrofuran / 1 h

12.1: 2.5 g / TBAF / tetrahydrofuran / 48 h / 50 °C

13.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

13.2: tetrahydrofuran; various solvent(s) / 0.5 h

13.3: 85 percent / HMPA / 24 h

14.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

With pyridine; 1H-imidazole; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; Phenylselenyl bromide; tetrabutyl ammonium fluoride; iodine; sodium hydride; diisobutylaluminium hydride; ozone; magnesium; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 5.1: Grignard reaction;
DOI:10.1021/ol026820t