(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

Base Information

Chemical Name:(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester
CAS No.:850416-15-8
Molecular Formula:C₄₃H₇₈O₈Si₂
Molecular Weight:779.259
Hs Code.:

(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

Synonyms:(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

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Chemical Property of (E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

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Technology Process of (E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

There total 14 articles about (E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl 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: 38.0%

: 850416-10-3
(2S,3S,4S)-2,4-Dimethyl-5-oxo-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

: 850416-14-7
[(4S,6S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-methoxymethoxy-2-oxo-octyl]-phosphonic acid diethyl ester

: 850416-15-8
(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃; for 26h;
DOI:10.1055/s-2005-862351

Reference yield:

: 64714-79-0
5-benzyloxy-3-oxo-pentanoic acid ethyl ester

: 850416-15-8
(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 82 percent / H₂ / {Ru[(S)-SYNPHOS]Br₂} / ethanol / 14 h / 80 °C / 8250.66 Torr

2.1: 86 percent / P₂O₅ / CHCl₃ / 0.25 h / 0 °C

3.1: LDA / tetrahydrofuran / -40 °C

3.2: 84 percent / tetrahydrofuran / 4.5 h / -40 °C

4.1: 93 percent / H₂ / Ikariya-Mashima's catalyst / methanol / 8 h / 20 °C / 60004.8 Torr

5.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

6.1: 85 percent / DIBALH / toluene / 0.42 h / -78 °C

7.1: n-BuLi / tetrahydrofuran / -78 °C

7.2: 87 percent / tetrahydrofuran / 0.42 h / -78 °C

8.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 0 - 20 °C

9.1: 38 percent / LiCl; DIPEA / acetonitrile / 26 h / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; hydrogen; phosphorus pentoxide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; RuBr₂[(S)-(C₆H₂OCH₂CH₂OP(C₆H₅)2)2]; Ikariya-Mashima's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; toluene; acetonitrile;
DOI:10.1055/s-2005-862351

Reference yield:

: 95112-81-5,113335-04-9
(S)-ethyl 5-benzyloxy-3-hydroxypentanoate

: 850416-15-8
(E)-(2S,3S,4R,9S,11S)-13-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-11-methoxymethoxy-2,4-dimethyl-7-oxo-3-triisopropylsilanyloxy-tridec-5-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / P₂O₅ / CHCl₃ / 0.25 h / 0 °C

2.1: LDA / tetrahydrofuran / -40 °C

2.2: 84 percent / tetrahydrofuran / 4.5 h / -40 °C

3.1: 93 percent / H₂ / Ikariya-Mashima's catalyst / methanol / 8 h / 20 °C / 60004.8 Torr

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -30 °C

5.1: 85 percent / DIBALH / toluene / 0.42 h / -78 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

6.2: 87 percent / tetrahydrofuran / 0.42 h / -78 °C

7.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 0 - 20 °C

8.1: 38 percent / LiCl; DIPEA / acetonitrile / 26 h / 20 °C

With 2,6-dimethylpyridine; n-butyllithium; hydrogen; phosphorus pentoxide; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; Ikariya-Mashima's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; acetonitrile;
DOI:10.1055/s-2005-862351