(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Base Information

Chemical Name:(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde
CAS No.:819066-91-6
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

Synonyms:

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Chemical Property of (4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

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Technology Process of (4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

There total 15 articles about (4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde 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:

: 132958-25-9
(3S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

: 819066-91-6
(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / 2,6-lutidine / dimethylformamide / 13 h / 20 °C

2: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

3: 51 percent / POCl₃ / pyridine / 48 h / 20 °C

4: n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

5: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

6: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

7: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

8: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

9: 90 percent / PPTS / CH₂Cl₂ / 10 h / Heating

10: 77 percent / Li; NH₃ / tetrahydrofuran / 0.33 h / -78 °C

11: 85 percent / Dess-Martin periodinane / CH₂Cl₂

12: 46 percent / DBU / 0.5 h / 90 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributyltin chloride; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium cyanoborohydride; potassium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 8: Tamao oxidation reaction;
DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 819066-91-6
(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

3: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

4: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

5: 90 percent / PPTS / CH₂Cl₂ / 10 h / Heating

6: 77 percent / Li; NH₃ / tetrahydrofuran / 0.33 h / -78 °C

7: 85 percent / Dess-Martin periodinane / CH₂Cl₂

8: 46 percent / DBU / 0.5 h / 90 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tributyltin chloride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium cyanoborohydride; potassium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 4: Tamao oxidation reaction;
DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

: (2R,4R)-6-Benzyloxymethyl-2-hydroxymethyl-5-methyl-3,4-dihydro-2H-pyran-4-ol

: 819066-91-6
(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

3: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

4: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

5: 90 percent / PPTS / CH₂Cl₂ / 10 h / Heating

6: 77 percent / Li; NH₃ / tetrahydrofuran / 0.33 h / -78 °C

7: 85 percent / Dess-Martin periodinane / CH₂Cl₂

8: 46 percent / DBU / 0.5 h / 90 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tributyltin chloride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium cyanoborohydride; potassium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 4: Tamao oxidation reaction;
DOI:10.1016/j.tetlet.2004.10.071