(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Base Information

Chemical Name:(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane
CAS No.:256659-04-8
Molecular Formula:C₂₂H₃₈O₄SSi
Molecular Weight:426.693
Hs Code.:

Synonyms:(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

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Chemical Property of (-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

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Technology Process of (-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

There total 6 articles about (-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane 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: 91.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 256659-03-7
(-)-[2R,4R,S(S)]-6-hydroxy-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

: 256659-04-8
(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

: 91796-57-5
(1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate

: 256659-04-8
(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 69 percent / NaH; tBuLi / pentane; tetrahydrofuran / 0.67 h / 0 °C

2: 47 percent / DIBAL-H / toluene; methanol / 1.75 h / -78 - 20 °C

3: 97 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 4 h / -78 °C

4: 97 percent / pTsOH / acetone / 3 h / 20 °C

5: 96 percent / DIBAL-H / toluene; tetrahydrofuran / 7 h / -78 °C

6: 91 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; diethyl methoxy borane; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; toluene; pentane; 1: Substitution / 2: Reduction / 3: Reduction / 4: Condensation / 5: Reduction / 6: silylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R

Reference yield:

: 218168-22-0
methyl (-)-(S)-3,5-dioxo-6-(p-tolylsulfinyl)hexanoate

: 256659-04-8
(-)-[2R,4R,S(S)]-6-(tert-butyldimethylsilyloxy)-syn-2,4-(isopropylidenedioxy)-1-(p-tolylsulfinyl)hexane

Guidance literature:: Multi-step reaction with 5 steps

1: 47 percent / DIBAL-H / toluene; methanol / 1.75 h / -78 - 20 °C

2: 97 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 4 h / -78 °C

3: 97 percent / pTsOH / acetone / 3 h / 20 °C

4: 96 percent / DIBAL-H / toluene; tetrahydrofuran / 7 h / -78 °C

5: 91 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; diethyl methoxy borane; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; toluene; 1: Reduction / 2: Reduction / 3: Condensation / 4: Reduction / 5: silylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<3021::AID-EJOC3021>3.0.CO;2-R