(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester
CAS No.:155434-33-6
Molecular Formula:C₄₅H₆₈O₉Si₂
Molecular Weight:809.201
Hs Code.:

(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

Synonyms:(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

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Chemical Property of (E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

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Technology Process of (E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

There total 26 articles about (E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-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:

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

: 155434-33-6
(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 24 steps

1: 100 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

2: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

3: benzene / 12 h / 80 °C

4: 95 percent / 1.0 M di-isobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 93 percent / (+)-DET, Ti(O-iPr)2, 3.0 M t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

6: 100 percent / SO₃*py complex, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / Ambient temperature

7: 94 percent / 1.0 M NaHMDS / tetrahydrofuran / 1 h / 0 °C

8: 97 percent / 1.0 M TBAF / tetrahydrofuran / 0.25 h / 0 °C

9: 53 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

10: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

11: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

12: benzene / 6.5 h / 80 °C

13: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

14: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

15: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

16: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

17: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

18: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

19: 35 percent KH / tetrahydrofuran / 0.5 h / Ambient temperature

20: AcOH, H₂O / tetrahydrofuran / 8 h / 60 °C

22: 99 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

23: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

24: benzene / 12 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; diisobutylaluminum hydride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; titanium(II) diisopropoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; potassium hydride; ozone; acetic acid; triethylamine; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

: 155434-13-2
(2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran

: 155434-33-6
(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 23 steps

1: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

2: benzene / 12 h / 80 °C

3: 95 percent / 1.0 M di-isobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

4: 93 percent / (+)-DET, Ti(O-iPr)2, 3.0 M t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

5: 100 percent / SO₃*py complex, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / Ambient temperature

6: 94 percent / 1.0 M NaHMDS / tetrahydrofuran / 1 h / 0 °C

7: 97 percent / 1.0 M TBAF / tetrahydrofuran / 0.25 h / 0 °C

8: 53 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

9: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

10: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

11: benzene / 6.5 h / 80 °C

12: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

13: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

14: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

15: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

16: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

17: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

18: 35 percent KH / tetrahydrofuran / 0.5 h / Ambient temperature

19: AcOH, H₂O / tetrahydrofuran / 8 h / 60 °C

21: 99 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

22: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

23: benzene / 12 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; diisobutylaluminum hydride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; titanium(II) diisopropoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; potassium hydride; ozone; acetic acid; triethylamine; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

: 155434-18-7
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

: 155434-33-6
(E)-3-[(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-8-Acetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 53 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

2: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

3: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

4: benzene / 6.5 h / 80 °C

5: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

6: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

7: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

8: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

9: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

10: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

11: 35 percent KH / tetrahydrofuran / 0.5 h / Ambient temperature

12: AcOH, H₂O / tetrahydrofuran / 8 h / 60 °C

14: 99 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

15: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

16: benzene / 12 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; potassium hydride; ozone; acetic acid; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;