(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester
CAS No.:221381-09-5
Molecular Formula:C₂₆H₃₄O₈
Molecular Weight:474.551
Hs Code.:

Synonyms:(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

There total 24 articles about (E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-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:

: 100-39-0
benzyl bromide

: 221381-09-5
(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 26 steps

1: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

4: benzene / 17 h / 25 °C

5: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

6: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

7: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

8: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

9: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

10: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

11: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

12: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

13: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

14: benzene / 11 h / 25 °C

15: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

16: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

17: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

18: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

19: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

20: imidazole / CH₂Cl₂ / 1 h / 0 °C

21: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

22: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

23: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

24: TBAF / tetrahydrofuran / 3 h / 25 °C

25: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

26: toluene / 5 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 122821-83-4
2,6-Anhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-D-altro-non-8-enitol

: 221381-09-5
(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 25 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

2: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

3: benzene / 17 h / 25 °C

4: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

5: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

6: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

7: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

8: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

9: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

10: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

11: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

12: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

13: benzene / 11 h / 25 °C

14: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

15: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

16: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

17: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

18: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

19: imidazole / CH₂Cl₂ / 1 h / 0 °C

20: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

21: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

22: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

23: TBAF / tetrahydrofuran / 3 h / 25 °C

24: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

25: toluene / 5 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

: 221380-90-1
(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-but-2-en-1-ol

: 221381-09-5
(E)-3-((4aR,5aS,6aR,8S,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 21 steps

1: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

2: Et₃N, SO₃*pyr / CH₂Cl₂; dimethylsulfoxide / 2 h

3: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 25 deg C, 1 h

4: TBAF / tetrahydrofuran / 1 h / -20 - 0 °C

5: imidazole / dimethylformamide; CH₂Cl₂ / 3 h / 0 °C

6: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 30 min

7: 1.) 9-BBN, 2.) H₂O₂, NaHCO₃, H₂O / 1.) THF, 0 deg C, 4 h, 2.) THF, 0 deg C, 4 h

8: SO₃*pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

9: benzene / 11 h / 25 °C

10: 88 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

11: 97 percent / 4 Angstroem molecular sieves, (+)-DET, Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 18 h / -25 °C

12: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

13: 1) NaHMDS / 1.) THF, 2.) THF, 0 deg C, 15 min

14: 26 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

15: imidazole / CH₂Cl₂ / 1 h / 0 °C

16: pyridinium p-toluenesulfonate, 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 25 °C

17: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 1 h, 2.) CH₂Cl₂, MeOH, 25 deg C, 2 h

18: pyridinium p-toluenesulfonate / CH₂Cl₂ / 28 h / 25 °C

19: TBAF / tetrahydrofuran / 3 h / 25 °C

20: Et₃N, SO₃*pyr / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

21: toluene / 5 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E