2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

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Chemical Name:2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester
CAS No.:288380-86-9
Molecular Formula:C₃₁H₅₄O₅SSi₂
Molecular Weight:595.004
Hs Code.:

2,4,6-trimethyl-benzenesulfonic acid 4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-[1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

Synonyms:2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

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Chemical Property of 2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

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Technology Process of 2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

There total 25 articles about 2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl 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:

: 55174-91-9
(-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose

: 288380-86-9
2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

Guidance literature:: Multi-step reaction with 21 steps

1.1: 98 percent / 4 Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

2.1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: 58 percent / 4 M HCl / toluene; dioxane / 16 h / 0 - 20 °C

4.1: PPh₃; azodicarboxylic acid diethyl ester / tetrahydrofuran; toluene / 3.25 h / 0 - 20 °C

5.1: 1.67 g / NaOH / methanol; H₂O / 1 h / 0 °C

6.1: 88 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 14 h / 0 - 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 50 °C

7.2: 85 percent / 3 M NaOH; 30percent H₂O₂ / H₂O; tetrahydrofuran / 2 h / 20 °C

8.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

9.1: H₂ / 20percent Pd(OH)2/C / ethanol / 12 h

9.2: 79 percent / LiHMDS / tetrahydrofuran / 0.67 h / 0 °C

10.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

11.1: 80 percent / nBuLi; BF₃*OEt₂ / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

12.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 - 20 °C

13.1: 85 percent / pyridine; CH₂Cl₂ / 5 h / 0 - 20 °C

14.1: 74 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 12 h / Heating

15.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

16.1: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

17.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

18.1: 263 mg / dimethylsulfoxide / 2 h / 70 °C

19.1: 85 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

20.1: 82 percent / NaBH₄ / methanol / 0.5 h / 0 °C

21.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; 20percent Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Wittig reaction / 4.1: Mitsunobu reaction;
DOI:10.1021/jo010375i

Reference yield:

: 55174-92-0
1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose

: 288380-86-9
2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 58 percent / 4 M HCl / toluene; dioxane / 16 h / 0 - 20 °C

3.1: PPh₃; azodicarboxylic acid diethyl ester / tetrahydrofuran; toluene / 3.25 h / 0 - 20 °C

4.1: 1.67 g / NaOH / methanol; H₂O / 1 h / 0 °C

5.1: 88 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 14 h / 0 - 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 50 °C

6.2: 85 percent / 3 M NaOH; 30percent H₂O₂ / H₂O; tetrahydrofuran / 2 h / 20 °C

7.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

8.1: H₂ / 20percent Pd(OH)2/C / ethanol / 12 h

8.2: 79 percent / LiHMDS / tetrahydrofuran / 0.67 h / 0 °C

9.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

10.1: 80 percent / nBuLi; BF₃*OEt₂ / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

11.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 - 20 °C

12.1: 85 percent / pyridine; CH₂Cl₂ / 5 h / 0 - 20 °C

13.1: 74 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 12 h / Heating

14.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

15.1: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

16.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

17.1: 263 mg / dimethylsulfoxide / 2 h / 70 °C

18.1: 85 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

19.1: 82 percent / NaBH₄ / methanol / 0.5 h / 0 °C

20.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; diethylazodicarboxylate; 20percent Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Wittig reaction / 3.1: Mitsunobu reaction;
DOI:10.1021/jo010375i

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 288380-86-9
2,4,6-trimethyl-benzenesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-3-[1-(tert-butyl-dimethyl-silanyloxy)-allyl]-hept-6-ynyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: 86 percent / pyridine / 10 h / 0 °C

2.1: 98 percent / 4 Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

3.1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 - 20 °C

4.1: 58 percent / 4 M HCl / toluene; dioxane / 16 h / 0 - 20 °C

5.1: PPh₃; azodicarboxylic acid diethyl ester / tetrahydrofuran; toluene / 3.25 h / 0 - 20 °C

6.1: 1.67 g / NaOH / methanol; H₂O / 1 h / 0 °C

7.1: 88 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 14 h / 0 - 20 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 50 °C

8.2: 85 percent / 3 M NaOH; 30percent H₂O₂ / H₂O; tetrahydrofuran / 2 h / 20 °C

9.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C

10.1: H₂ / 20percent Pd(OH)2/C / ethanol / 12 h

10.2: 79 percent / LiHMDS / tetrahydrofuran / 0.67 h / 0 °C

11.1: 84 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

12.1: 80 percent / nBuLi; BF₃*OEt₂ / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

13.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 - 20 °C

14.1: 85 percent / pyridine; CH₂Cl₂ / 5 h / 0 - 20 °C

15.1: 74 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 12 h / Heating

16.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

17.1: 96 percent / DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -78 °C

18.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

19.1: 263 mg / dimethylsulfoxide / 2 h / 70 °C

20.1: 85 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

21.1: 82 percent / NaBH₄ / methanol / 0.5 h / 0 °C

22.1: DMAP / CH₂Cl₂ / 12 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; 20percent Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: Wittig reaction / 5.1: Mitsunobu reaction;
DOI:10.1021/jo010375i