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

Base Information

• Chemical Name: (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester
• CAS No.: 632339-38-9
• Molecular Formula: C₃₆H₅₆O₅Si₂
• Molecular Weight: 625.009
• Mol file: 632339-38-9.mol

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

Chemical Property of (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester

There total 16 articles about (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl 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: 87.0%

ethyl 2-[bis(o-isopropylphenoxy)phosphinyl]propionate (216519-86-7) + 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde (632339-36-7) → (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester (632339-38-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1055/s-2003-40856

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester (632339-38-9)

Guidance literature:

Multi-step reaction with 16 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

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; 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; 1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation / 15: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → (Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester (632339-38-9)

Guidance literature:

Multi-step reaction with 15 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

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; 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; 4: Dess-Martin oxidation / 14: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

upstream raw materials:

ethyl 2-[bis(o-isopropylphenoxy)phosphinyl]propionate

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

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

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

Downstream raw materials:

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-propenal

(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

(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

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