(4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

Base Information

Chemical Name:(4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol
CAS No.:111264-67-6
Molecular Formula:C₂₄H₃₂O₆
Molecular Weight:416.514
Hs Code.:

Synonyms:

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Chemical Property of (4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

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Technology Process of (4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

There total 16 articles about (4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol 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:

: 106540-42-5
dimethyl (1R,4aR,6S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate

: 111264-67-6
(4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

Guidance literature:: Multi-step reaction with 15 steps

1: imidazole / dimethylformamide / 20 h / Ambient temperature

2: 1.) (i-Bu)2AlH, 2.) methanol / 1.) toluene, -63 deg C, 50 min, 2.) room temp., 2 h

3: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 74 percent / H₂ / 10percent palladium-carbon / ethyl acetate / Ambient temperature

5: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg. C, 1 h, 2.) temp. up to 0 deg C

6: 2-methyl-2-butene, sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 2 h / Ambient temperature

7: 2.) 46percent hydrofluoric acid / 1.) ether, 2.) acetonitrile, room temp., 2 h.

8: 97 percent / pyridine / 41 h / Ambient temperature

9: 77 percent / (n-Bu)4NBr, DBU / dimethylformamide / 44 h / 90 °C

10: 21 percent / OsO₄, pyridine / tetrahydrofuran / 72 h / Ambient temperature

11: p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

12: 56 percent / LiAlH₄ / diethyl ether / 0 deg C, 2 h, room temp., 12 h.

13: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) THF, -20 deg C, 2 h

15: 2N HCl / propan-2-ol; tetrahydrofuran / 21 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; methanol; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen fluoride; tetrabutylammomium bromide; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol;

Reference yield:

: 111161-33-2
dimethyl (1R,4aR,6S,8aS)-6-(tert-butyldimethylsilyloxy)-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxylate

: 111264-67-6
(4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) (i-Bu)2AlH, 2.) methanol / 1.) toluene, -63 deg C, 50 min, 2.) room temp., 2 h

2: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 74 percent / H₂ / 10percent palladium-carbon / ethyl acetate / Ambient temperature

4: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg. C, 1 h, 2.) temp. up to 0 deg C

5: 2-methyl-2-butene, sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 2 h / Ambient temperature

6: 2.) 46percent hydrofluoric acid / 1.) ether, 2.) acetonitrile, room temp., 2 h.

7: 97 percent / pyridine / 41 h / Ambient temperature

8: 77 percent / (n-Bu)4NBr, DBU / dimethylformamide / 44 h / 90 °C

9: 21 percent / OsO₄, pyridine / tetrahydrofuran / 72 h / Ambient temperature

10: p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

11: 56 percent / LiAlH₄ / diethyl ether / 0 deg C, 2 h, room temp., 12 h.

12: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) THF, -20 deg C, 2 h

14: 2N HCl / propan-2-ol; tetrahydrofuran / 21 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen fluoride; tetrabutylammomium bromide; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol;

Reference yield:

: 111161-37-6
(5aR,7S,9aS,9bS)-(-)-(tert-butyldimethylsilyloxy)-5,5a,6,7,8,9,9a,9b-octahydro-6,6,9a-trimethylnaphtho<1,2-c>furan-1(3H)-one

: 111264-67-6
(4aR,6S,7R,8aS)-(+)-1-<(3,4-diformyl-2-hydroxy-6-methoxyphenyl)methyl>-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-6,7-naphthalenediol

Guidance literature:: Multi-step reaction with 13 steps

1: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2: 74 percent / H₂ / 10percent palladium-carbon / ethyl acetate / Ambient temperature

3: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg. C, 1 h, 2.) temp. up to 0 deg C

4: 2-methyl-2-butene, sodium chlorite, sodium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 2 h / Ambient temperature

5: 2.) 46percent hydrofluoric acid / 1.) ether, 2.) acetonitrile, room temp., 2 h.

6: 97 percent / pyridine / 41 h / Ambient temperature

7: 77 percent / (n-Bu)4NBr, DBU / dimethylformamide / 44 h / 90 °C

8: 21 percent / OsO₄, pyridine / tetrahydrofuran / 72 h / Ambient temperature

9: p-toluenesulfonic acid / acetone / 4 h / Ambient temperature

10: 56 percent / LiAlH₄ / diethyl ether / 0 deg C, 2 h, room temp., 12 h.

11: 1.) methanesulfonyl chloride, triethylamine, 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) THF, -20 deg C, 2 h

13: 2N HCl / propan-2-ol; tetrahydrofuran / 21 h / Ambient temperature

With pyridine; hydrogenchloride; sodium chlorite; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen fluoride; tetrabutylammomium bromide; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol;