4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde
CAS No.:632339-36-7
Molecular Formula:C₃₁H₄₈O₄Si₂
Molecular Weight:540.891
Hs Code.:

4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[2-(<i>tert</i>-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

Synonyms:4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

There total 15 articles about 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-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: 95.0%

: 632339-34-5
{4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-methanol

: 632339-36-7
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 25 ℃;
DOI:10.1055/s-2003-40856

Reference yield:

: 89956-14-9
[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

: 632339-36-7
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1: 90 percent / Red-Al / diethyl ether / -20 °C

2: 95 percent / PPTS / 25 °C

3: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

4: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

5: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

6: 95 percent / Dowex / methanol; H₂O / Heating

7: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

8: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

9: TsOH*H₂O / CH₂Cl₂ / 25 °C

10: 90 percent / 2,6-lutidine / dimethylformamide / 25 °C

11: 89 percent / n-BuLi / tetrahydrofuran / -78 °C

12: 84 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / -78 - -30 °C

13: 82 percent / H₂ / Pd/C / ethanol / 25 °C

14: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; lithium hydroxide; n-butyllithium; dowex; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4: Dess-Martin oxidation / 14: Dess-Martin oxidation;
DOI:10.1055/s-2003-40856

Reference yield:

: 89923-31-9
(E)-5-(benzyloxy)pent-2-en-1-ol

: 632339-36-7
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 15 steps

1: 91 percent / D-(-)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

2: 90 percent / Red-Al / diethyl ether / -20 °C

3: 95 percent / PPTS / 25 °C

4: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

5: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

6: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

7: 95 percent / Dowex / methanol; H₂O / Heating

8: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

9: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

10: TsOH*H₂O / CH₂Cl₂ / 25 °C

11: 90 percent / 2,6-lutidine / dimethylformamide / 25 °C

12: 89 percent / n-BuLi / tetrahydrofuran / -78 °C

13: 84 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / -78 - -30 °C

14: 82 percent / H₂ / Pd/C / ethanol / 25 °C

15: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; dmap; lithium hydroxide; n-butyllithium; dowex; diethyl (2S,3S)-tartrate; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation / 15: Dess-Martin oxidation;
DOI:10.1055/s-2003-40856