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

Base Information

Chemical Name:(1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide
CAS No.:95218-58-9
Molecular Formula:C₃₄H₄₀O₃P*I
Molecular Weight:654.568
Hs Code.:

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

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

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

There total 15 articles about (1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide 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: 55.0%

: 95218-57-8
(1SR,2SR,8SR,8aRS)-1-(iodomethyl)-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

: 95218-63-6
(2aS,3S,8aS,8bR)-3-Methyl-2a,3,7,8,8a,8b-hexahydro-2H-naphtho[1,8-bc]furan

: 95218-58-9
(1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide

Guidance literature:: With triphenylphosphine; In tetrahydrofuran; at 100 ℃; for 10h;
DOI:10.1021/jo00208a010

Reference yield: 55.0%

: 95218-57-8
(1SR,2SR,8SR,8aRS)-1-(iodomethyl)-8-<(2-methoxyethoxy)methoxy>-2-methyl-1,2,6,7,8,8a-hexahydronaphthalene

: 603-35-0
triphenylphosphine

: 95218-63-6
(2aS,3S,8aS,8bR)-3-Methyl-2a,3,7,8,8a,8b-hexahydro-2H-naphtho[1,8-bc]furan

: 95218-58-9
(1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide

Guidance literature:: In tetrahydrofuran; at 100 ℃; for 13h;
DOI:10.1021/jo00208a010

Reference yield:

: 85539-94-2,95341-08-5,95341-09-6
(4SR,5SR)-4-carbethoxy-3-methoxy-5-methyl-1-<(trimethylsilyl)oxy>cyclohexene

: 95218-58-9
(1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) LiAlH₄, 2.) aq. NaOH / 1.) ether, from -78 deg C to -20 deg C, 2 h, 2.) RT, 1.5 h

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

3: 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

4: 74 percent / aq. HCl / methanol / 0.75 h / Heating

5: 95 percent / DMAP, triethylamine / CH₂Cl₂ / 8 h / Ambient temperature

6: 81 percent / conc. HCl / methanol / 0.5 h

7: 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

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

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

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

11: 91 percent / N,N-diisopropylethylamine, DMAP / CH₂Cl₂ / 22 h

12: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 7 h / Ambient temperature

13: CH₂Cl₂ / 4 h / 0 °C

14: 1.80 mg / tetrabutylammonium iodide / tetrahydrofuran / 2.25 h / Heating

15: 55 percent / triphenylphosphine / tetrahydrofuran / 10 h / 100 °C

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