[3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane
• CAS No.: 221381-12-0
• Molecular Formula: C₄₁H₅₄O₇Si
• Molecular Weight: 686.961

Synonyms:[3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane

Chemical Property of [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane

There total 31 articles about [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane 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:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-82-3) → [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane (221381-12-0)

Guidance literature:

Multi-step reaction with 29 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

27: H₂ / Raney-Nickel W₂

28: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

29: imidazole / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; Raney-Nickel W₂; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; 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:

2,6-Anhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-D-altro-non-8-enitol (122821-83-4) → [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane (221381-12-0)

Guidance literature:

Multi-step reaction with 28 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

26: H₂ / Raney-Nickel W₂

27: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

28: imidazole / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; Raney-Nickel W₂; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; 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:

benzyl bromide (100-39-0) → [3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propoxy]-tert-butyl-diphenyl-silane (221381-12-0)

Guidance literature:

Multi-step reaction with 29 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

27: H₂ / Raney-Nickel W₂

28: LiAlH₄ / diethyl ether / 1.5 h / 0 °C

29: imidazole / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ozone; triethylamine; triphenylphosphine; Raney-Nickel W₂; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; 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

upstream raw materials:

tert-butylchlorodiphenylsilane

3-((4aR,5aS,6aR,8R,10S,10aS,11aR,12aS)-10-Benzyloxy-2,2-dimethyl-dodecahydro-1,3,5,7,11-pentaoxa-naphthacen-8-yl)-propan-1-ol

benzyl bromide

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

Downstream raw materials:

(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene-2-carbaldehyde

{(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-methanol

(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-octahydro-1,8,10-trioxa-anthracen-3-one

(2R,3S,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-decahydro-1,8,10-trioxa-anthracen-3-ol

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