(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

Base Information

Chemical Name:(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal
CAS No.:850416-13-6
Molecular Formula:C₂₂H₃₈O₅Si
Molecular Weight:410.626
Hs Code.:

Synonyms:(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

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Chemical Property of (3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

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Technology Process of (3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

There total 6 articles about (3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal 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: 85.0%

: 850416-20-5
7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanoic acid tert-butyl ester

: 850416-13-6
(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.416667h;
DOI:10.1055/s-2005-862351

Reference yield:

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

: 850416-13-6
(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 850416-13-6
(3S,5S)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-heptanal

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; hydrogen; phosphorus pentoxide; diisobutylaluminium hydride; lithium diisopropyl amide; Ikariya-Mashima's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;
DOI:10.1055/s-2005-862351