(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

Base Information

Chemical Name:(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol
CAS No.:189232-06-2
Molecular Formula:C₂₁H₂₈O₃S
Molecular Weight:360.518
Hs Code.:

Synonyms:(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

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Chemical Property of (2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

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Technology Process of (2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

There total 11 articles about (2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol 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: 70.0%

: 189232-05-1
C₂₁H₂₈O₃S

: 189232-06-2
(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

Guidance literature:: With aluminum isopropoxide; In toluene; at 110 ℃; for 120h;
DOI:10.1016/S0040-4039(97)00475-9

Reference yield:

: 189232-12-0
(R)-2,5-Dimethyl-cyclopent-1-enecarboxylic acid ethyl ester

: 189232-06-2
(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: DIBA-H / hexane / 3 h / -78 °C

2: (COCl)2 / dimethylformamide / 2.5 h / 0 °C

3: 70 percent / ZnCl₂ / CH₂Cl₂ / 4 h / -50 - 0 °C

4: tetrahydrofuran / 1 h / -78 - -20 °C

5: NEt₃ / CH₂Cl₂ / 3 h / -78 deg C to r.t.

6: 85 percent / CaCO₃ / 1,2-dichloro-benzene / 3 h / 130 °C

7: 96 percent / MCPBA / CH₂Cl₂ / 4 h / -78 deg C to r.t.

8: 70 percent / Al(i-OPr)3 / toluene / 120 h / 110 °C

With oxalyl dichloride; aluminum isopropoxide; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; zinc(II) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; toluene;
DOI:10.1016/S0040-4039(97)00475-9

Reference yield:

: 189232-03-9
3-((R)-2,5-Dimethyl-cyclopent-1-enyl)-2,2-dimethyl-propionaldehyde

: 189232-06-2
(2R,4R,5S)-4,8,8-Trimethyl-1-methylene-6-(toluene-4-sulfonylmethyl)-spiro[4.4]non-6-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 1 h / -78 - -20 °C

2: NEt₃ / CH₂Cl₂ / 3 h / -78 deg C to r.t.

3: 85 percent / CaCO₃ / 1,2-dichloro-benzene / 3 h / 130 °C

4: 96 percent / MCPBA / CH₂Cl₂ / 4 h / -78 deg C to r.t.

5: 70 percent / Al(i-OPr)3 / toluene / 120 h / 110 °C

With aluminum isopropoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene; toluene;
DOI:10.1016/S0040-4039(97)00475-9