methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

Base Information

Chemical Name:methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate
CAS No.:71886-97-0
Molecular Formula:C₂₂H₃₀O₆S
Molecular Weight:422.543
Hs Code.:

Synonyms:methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

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Chemical Property of methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

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Technology Process of methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

There total 12 articles about methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-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: 99.0%

: 67-56-1
methanol

: 71886-95-8
trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-4a-(tosyloxymethyl)-6α-tris(methylthio)methylnaphthalen-6β-ol

: 71886-97-0
methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

Guidance literature:: With mercury dichloride; mercury(II) oxide; In water; for 4h; Ambient temperature;
DOI:10.1021/jo01290a005

Reference yield:

: 33214-69-6
3,4-dihydro-1,1-dimethyl-6-methoxy-2(1H)-naphthalenone

: 71886-97-0
methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 97.4 percent / Li/NH₃(l) / diethyl ether / 0.5 h

2: 1.) conc. HCl, 2.) triethylaluminum / 1.) THF, 2 h, 2.) THF, hexane, 0 deg C, 2h.

3: 97.4 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / Heating

4: 99.1 percent / phenyltrimethylammonium perbromide / CH₂Cl₂

5: 93 percent / DBU / 1.) 120-150 deg C, 1.5 h, 2.) 150 deg C, 0.5 h.

6: 1.) LiAlH₄, 2.) 5percent acetic acid

7: 98 percent / NaBH₄ / aq. ethanol / 1.) room temperature, 10 min, 2.) 30-70 deg C, 1 h, 3.) reflux, 1 h.

8: n-butyllithium / tetrahydrofuran

9: 89 percent / 3.5percent HClO₄ / tetrahydrofuran / 1.5 h / 0 - 5 °C

10: 1.63 g / n-butyllithium / tetrahydrofuran / 1 h / -70 - -65 °C

11: 99 percent / HgO, HgCl₂ / H₂O / 4 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; ammonia; triethylaluminum; phenyltrimethylammonium tribromide; lithium; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene;
DOI:10.1021/jo01290a005

Reference yield:

: 71886-83-4
6-methoxy-1,1-dimethyl-3,4-dihydronaphthalene-2(1H)-one

: 71886-97-0
methyl trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-6β-hydroxy-4a-(tosyloxymethyl)naphthalene-6-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: 90.3 percent / 97percent hydrazine, 85percent KOH / ethane-1,2-diol / 1.) 130 deg C, 1 h, 2.) reflux , 21 h.

2: 97.4 percent / Li/NH₃(l) / diethyl ether / 0.5 h

3: 1.) conc. HCl, 2.) triethylaluminum / 1.) THF, 2 h, 2.) THF, hexane, 0 deg C, 2h.

4: 97.4 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / Heating

5: 99.1 percent / phenyltrimethylammonium perbromide / CH₂Cl₂

6: 93 percent / DBU / 1.) 120-150 deg C, 1.5 h, 2.) 150 deg C, 0.5 h.

7: 1.) LiAlH₄, 2.) 5percent acetic acid

8: 98 percent / NaBH₄ / aq. ethanol / 1.) room temperature, 10 min, 2.) 30-70 deg C, 1 h, 3.) reflux, 1 h.

9: n-butyllithium / tetrahydrofuran

10: 89 percent / 3.5percent HClO₄ / tetrahydrofuran / 1.5 h / 0 - 5 °C

11: 1.63 g / n-butyllithium / tetrahydrofuran / 1 h / -70 - -65 °C

12: 99 percent / HgO, HgCl₂ / H₂O / 4 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; ammonia; triethylaluminum; phenyltrimethylammonium tribromide; lithium; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethylene glycol; toluene;
DOI:10.1021/jo01290a005