(2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol

Base Information

• Chemical Name: (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol
• CAS No.: 632339-43-6
• Molecular Formula: C₃₆H₅₆O₄Si₂
• Molecular Weight: 609.009
• Mol file: 632339-43-6.mol

Synonyms:(2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol

Chemical Property of (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol

There total 17 articles about (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-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: 81.0%

(2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester (632339-42-5) → (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol (632339-43-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1055/s-2003-40856

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol (632339-43-6)

Guidance literature:

Multi-step reaction with 19 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

15: 87 percent / DBU; NaI / tetrahydrofuran / -78 - 0 °C

16: 99 percent / DIBALH / CH₂Cl₂ / -78 °C

17: 99 percent / MnO₂ / CH₂Cl₂; benzene / 25 °C

18: 83 percent / toluene / Heating

19: 81 percent / DIBALH / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; manganese(IV) oxide; lithium hydroxide; n-butyllithium; dowex; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 4: Dess-Martin oxidation / 14: Dess-Martin oxidation / 18: Wittig reaction;

DOI:10.1055/s-2003-40856

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dien-1-ol (632339-43-6)

Guidance literature:

Multi-step reaction with 20 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

16: 87 percent / DBU; NaI / tetrahydrofuran / -78 - 0 °C

17: 99 percent / DIBALH / CH₂Cl₂ / -78 °C

18: 99 percent / MnO₂ / CH₂Cl₂; benzene / 25 °C

19: 83 percent / toluene / Heating

20: 81 percent / DIBALH / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; 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; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation / 15: Dess-Martin oxidation / 19: Wittig reaction;

DOI:10.1055/s-2003-40856

upstream raw materials:

(2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

(E)-5-(benzyloxy)pent-2-en-1-ol

(S)-5-phenylmethoxypentane-1,3-diol

Downstream raw materials:

2,2-Dimethyl-propionic acid (2E,4Z)-5-{(2R,3S,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienyl ester