2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

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Chemical Name:2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran
CAS No.:188539-95-9
Molecular Formula:C₃₂H₅₀O₄S
Molecular Weight:530.813
Hs Code.:

Synonyms:2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

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Chemical Property of 2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

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Technology Process of 2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

There total 9 articles about 2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran 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:

: 110-87-2
3,4-dihydro-2H-pyran

: 188539-95-9
2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 92.7 percent / TsOH / CH₂Cl₂ / 1 h / 0 °C

2: 96.2 percent / LiAlH₄

3: 1.) LiCl, NaHCO₃, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h

4: dimethylformamide / 12 h / Ambient temperature

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium chloride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)00103-8

Reference yield:

: 13017-23-7
(4aR,6aS,10aS,10bR)-(-)-2,3,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-4a,7,7,10a-tetramethyl-naphtho<2,1-b>pyran-3-ol

: 188539-95-9
2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 90.1 percent / benzene / 15 h / 70 °C

2: 92.7 percent / TsOH / CH₂Cl₂ / 1 h / 0 °C

3: 96.2 percent / LiAlH₄

4: 1.) LiCl, NaHCO₃, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h

5: dimethylformamide / 12 h / Ambient temperature

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium chloride; In dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(97)00103-8

Reference yield:

: 188539-96-0
Methanesulfonic acid (1S,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ylmethyl ester

: 188539-95-9
2-{(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-1-[(E)-4-methyl-5-(toluene-4-sulfonyl)-pent-3-enyl]-decahydro-naphthalen-2-yloxy}-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaOMe, 2.) 18-crown-6 / 1) MeOH, 30 deg C, 30 min; 2) MeOH, HMPA, 68 deg C, 12 h

2: 92.1 percent / KOH / ethanol / 1.5 h / 55 °C

3: 71.1 percent / DIBAL / toluene / 1 h / -65 °C

4: 90.1 percent / benzene / 15 h / 70 °C

5: 92.7 percent / TsOH / CH₂Cl₂ / 1 h / 0 °C

6: 96.2 percent / LiAlH₄

7: 1.) LiCl, NaHCO₃, 2,6-lutidine, 2.) MsCl / 1) DMF, 0 deg C, 50 min; 2) DMF, 0 deg C, 2.5 h

8: dimethylformamide / 12 h / Ambient temperature

With 2,6-dimethylpyridine; potassium hydroxide; lithium aluminium tetrahydride; 18-crown-6 ether; sodium methylate; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4020(97)00103-8