(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

Base Information

Chemical Name:(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene
CAS No.:95218-59-0
Molecular Formula:C₂₂H₃₀O₅S
Molecular Weight:406.543
Hs Code.:

Synonyms:(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

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Chemical Property of (1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

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Technology Process of (1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

There total 13 articles about (1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene 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: 53.0%

: 873-55-2
sodium benzenesulfonate

: 95218-56-7
(1SR,2SR,8SR,8aRS)-1-<<(methylsulfonyl)oxy>methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

: 95218-59-0
(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

Guidance literature:: With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 7h; Heating;
DOI:10.1021/jo00208a010

Reference yield: 26.0%

: 873-55-2
sodium benzenesulfonate

: 95218-56-7
(1SR,2SR,8SR,8aRS)-1-<<(methylsulfonyl)oxy>methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

: 95218-64-7
(1R,7R,8R,8aS)-8-Bromomethyl-1-(2-methoxy-ethoxymethoxy)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalene

: 95218-59-0
(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

Guidance literature:: With tetrabutylammomium bromide; In tetrahydrofuran; for 1h; Heating;
DOI:10.1021/jo00208a010

Reference yield:

: 95218-47-6,130695-73-7
(4R,5R)-4-Hydroxymethyl-5-methyl-cyclohex-2-enone

: 95218-59-0
(1SR,2SR,8SR,8aRS)-1-<(phenylsulfonyl)methyl>-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

Guidance literature:: Multi-step reaction with 13 steps

1: triethylamine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 27 h / Ambient temperature

2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -78 deg C to -20 deg C, 135 min, 2.) -78 deg C, 7.5 h

3: 74 percent / aq. HCl / methanol / 0.75 h / Heating

4: 95 percent / DMAP, triethylamine / CH₂Cl₂ / 8 h / Ambient temperature

5: 81 percent / conc. HCl / methanol / 0.5 h

6: 1.) N,N,N',N'-tetramethylethylenediamine (TMEDA), n-BuLi, 2.) aq. NH₄Cl / 1.) hexane, from -78 deg C to 0 deg C, 75 min, 2.) 0 deg C, 30 min

7: triethylamine, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

8: AgNO₃, N-chlorosuccinimide (NCS), 2,4,6-collidine / acetonitrile; H₂O; tetrahydrofuran / 0.08 h

9: 1.) L-selectride, 2.) aq. NaOH, H₂O₂ / 1.) THF, from -78 deg C to RT, 8.75 h, 2.) RT, 1 h

10: 91 percent / N,N-diisopropylethylamine, DMAP / CH₂Cl₂ / 22 h

11: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 7 h / Ambient temperature

12: CH₂Cl₂ / 4 h / 0 °C

13: 26 percent / tetrabutylammonium bromide / tetrahydrofuran / 1 h / Heating

With 2,4,6-trimethyl-pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; N-chloro-succinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; dihydrogen peroxide; L-Selectride; ammonium chloride; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00208a010