(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester
CAS No.:132375-78-1
Molecular Formula:C₄₁H₅₂O₈Si
Molecular Weight:700.945
Hs Code.:

(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

Synonyms:(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

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Chemical Property of (E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

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Technology Process of (E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

There total 27 articles about (E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl 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: 80.0%

: 132375-77-0
(E)-3-((2S,3S)-3-{(3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl}-oxiranyl)-acrylic acid methyl ester

: 132375-78-1
(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 0 - 25 ℃;

Reference yield:

: 132375-57-6
(3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

: 132375-78-1
(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 25 steps

1: CH₂Cl₂ / 18 h / 25 °C

2: 1) L-selectride, t-BuOH, 2) NaOH, H₂O₂ / 1) THF, -78 deg C, 1 h, 2) 0 deg C, 1 h

3: DIBAH / CH₂Cl₂ / 1 h / -78 °C

4: 95 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

5: 90 percent / camphersulfonic acid / methanol / 4 h / 25 °C

6: 1) n-Bu₂SnO, 2) CsF / 1) MeOH, 65 deg C, 1 h, 2) DMF, 25 deg C, 18 h

7: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

8: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C

9: benzene / 12 h / 25 °C

10: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

11: 92 percent / (+)-DET, Ti(IOPr)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 48 h / -20 °C

12: SO₃*Py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

13: NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

14: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 - 0 °C

15: 80 percent / camphersulfonic acid / CH₂Cl₂ / 2 h / 0 °C

16: 99 percent / imidazole / dimethylformamide / 12 h / 25 °C

17: 1) 9-BBN, 2) NaOH, H₂O₂ / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 1 h

18: oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

19: benzene / 12 h / 25 °C

20: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

21: 92 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 12 h / -20 °C

22: SO₃*py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

23: benzene / 12 h / 25 °C

24: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

25: 80 percent / camphersulfonic acid / CH₂Cl₂ / 0 - 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; L-Selectride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

: 132375-56-5
((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

: 132375-78-1
(E)-3-{(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-decahydro-1,8,10-trioxa-anthracen-2-yl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 26 steps

1: oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

2: CH₂Cl₂ / 18 h / 25 °C

3: 1) L-selectride, t-BuOH, 2) NaOH, H₂O₂ / 1) THF, -78 deg C, 1 h, 2) 0 deg C, 1 h

4: DIBAH / CH₂Cl₂ / 1 h / -78 °C

5: 95 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

6: 90 percent / camphersulfonic acid / methanol / 4 h / 25 °C

7: 1) n-Bu₂SnO, 2) CsF / 1) MeOH, 65 deg C, 1 h, 2) DMF, 25 deg C, 18 h

8: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

9: 1) ozone, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C

10: benzene / 12 h / 25 °C

11: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

12: 92 percent / (+)-DET, Ti(IOPr)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 48 h / -20 °C

13: SO₃*Py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1 h / 0 °C

14: NaN(TMS)2 / tetrahydrofuran / 1 h / 0 °C

15: 92 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / -20 - 0 °C

16: 80 percent / camphersulfonic acid / CH₂Cl₂ / 2 h / 0 °C

17: 99 percent / imidazole / dimethylformamide / 12 h / 25 °C

18: 1) 9-BBN, 2) NaOH, H₂O₂ / 1) THF, 0 deg C, 2 h, 2) 0 deg C, 1 h

19: oxalyl chloride, DMSO, NEt₃ / CH₂Cl₂ / 1 h / -78 °C

20: benzene / 12 h / 25 °C

21: 96 percent / DIBAH / CH₂Cl₂ / 1 h / -78 °C

22: 92 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieve / CH₂Cl₂ / 12 h / -20 °C

23: SO₃*py, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

24: benzene / 12 h / 25 °C

25: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

26: 80 percent / camphersulfonic acid / CH₂Cl₂ / 0 - 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; L-Selectride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;