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

Base Information

Chemical Name:Acetic acid (2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester
CAS No.:155434-21-2
Molecular Formula:C₄₃H₆₆O₇Si₂
Molecular Weight:751.164
Hs Code.:

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

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

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

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

There total 24 articles about Acetic acid (2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl 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: 99.0%

: 108-24-7
acetic anhydride

: 155434-31-4
(2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

: 155434-21-2
Acetic acid (2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 25 ℃;
DOI:10.1039/c39930001638

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

: 155434-21-2
Acetic acid (2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Guidance literature:: Multi-step reaction with 22 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

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:

: 155434-19-8
(2R,3S,4aR,6S,8S,8aS)-8-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 155434-21-2
Acetic acid (2S,4S,4aR,5aR,8S,9R,10aS,11aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5a-methyl-4-triisopropylsilanyloxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

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

3: benzene / 6.5 h / 80 °C

4: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

5: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

6: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

7: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

8: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

9: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

10: 35 percent KH / tetrahydrofuran / 0.5 h / Ambient temperature

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

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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 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;