(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:111161-36-5
Molecular Formula:C₂₃H₃₂O₅S
Molecular Weight:420.57
Hs Code.:

(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 9 articles about (1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 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: 97.0%

: 10247-03-7
methyl (1S,4aR,6S,8aS)-(+)-1,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-2,5,5,8a-tetramethyl-1-naphthalenecarboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 111161-36-5
(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: With pyridine; for 41h; Ambient temperature;

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

: 111161-36-5
(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; methanol; sodium chlorite; lithium aluminium tetrahydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; 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

: 111161-36-5
(1S,4aR,6S,8aS)-2,5,5,8a-Tetramethyl-6-(toluene-4-sulfonyloxy)-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

With pyridine; methanol; sodium chlorite; lithium aluminium tetrahydride; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In diethyl ether; water; ethyl acetate; tert-butyl alcohol;